Piperidine,3-phenyl-, (3R)-
- CAS Number:430461-56-6
- Molecular Formula:C11H15N
- Molecular Weight:161.247
- Mol File:430461-56-6.mol
Synonyms:(R)-3-Phenylpiperidine;
Physicochemical Properties
- Melting Point:179-181℃
- Boiling Point:263.183 °C at 760 mmHg
- Density:0.967 g/cm3
- Solubility:N/A
- Flash Point:115.488 °C
- Vapor Density:N/A
- Refractive Index:1.522
- Sensitive:N/A
- Storage Temp.:N/A
- Appearance/Colour:N/A
Piperidine,3-phenyl-, (3R)- Safety information and MSDS
·Hazard identification:
| Pictogram(s) |  |
|---|---|
| Signal word | Warning |
| Hazard statement(s) | H302 Harmful if swallowed H312 Harmful in contact with skin H315 Causes skin irritation H319 Causes serious eye irritation H332 Harmful if inhaled H335 May cause respiratory irritation |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. |
| Response | P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/…if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P312 Call a POISON CENTER/doctor/…if you feel unwell. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P332+P313 If skin irritation occurs: Get medical advice/attention. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. |
| Storage | P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up. |
| Disposal | P501 Dispose of contents/container to ... |
·Composition/information on ingredients:
| Chemical name | Common names and synonyms | CAS number | EC number | Concentration |
|---|---|---|---|---|
| (R)-3-Phenylpiperidine | (R)-3-Phenylpiperidine | 430461-56-6 | none | 100% |
·First-aid measures:
General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
·Fire-fighting measures:
Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.
·Accidental release measures:
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.
Piperidine,3-phenyl-, (3R)- Relevant articles
All total 4 Articles be found
All total 4 Articles be foundSynthesis method for (R)-3-phenylpiperidine or/and (S)-3-phenylpiperidine and synthesis method for chiral intermediate of niraparib
-
, (2018/07/10)
The invention belongs to the technical field of organic synthesis. The synthesis method firstly provided by the invention takes benzyl-4-oxopiperidine as a starting material, and the starting materialis subjected to Grignard reaction, elimination reaction, hydrogenation reduction reaction and chiral resolution in sequence to successfully obtain a target product (R)-3-phenylpiperidine or/ and (S)-3-phenylpiperidine. The synthesis method sencondly provided by the invention takes the same starting raw material for Grignard reaction, organic silicon reagent is used for removing a hydroxide radical, and benzyl is removed by catalytic hydrogenation reaction; finally, the chiral resolution is carried out to obtain a target product. The (S)-3-phenylpiperidine can be synthesized according to the synthesis method. (S)-3-p-aminosalicylic phenylpiperidine can be synthesized according to the third aspect; or according to the fourth aspect, (S)-3-p-bromophenyl piperidine is synthesized to serve asthe key intermediate for preparing the niraparib. According to the synthesis method for (R)-3-phenylpiperidine or/ and (S)-3-phenylpiperidine and the synthesis method for chiral intermediate of niraparib, production cost is obviously lowered, and the synthesis methods are favorable for the large-scale industrial production of a niraparib medicine.
Pd-catalyzed asymmetric allylic alkylation with nitromethane using a chiral diaminophosphine oxide: (S,RP)-Ph-DIAPHOX. Enantioselective synthesis of (R)-preclamol and (R)-baclofen
Nemoto, Tetsuhiro,Jin, Long,Nakamura, Hiroshi,Hamada, Yasumasa
, p. 6577 - 6581 (2007/10/03)
A Pd-catalyzed asymmetric allylic alkylation with nitromethane using an aspartic acid-derived P-chirogenic diaminophosphine oxide [(S,RP)-Ph-DIAPHOX] is described. This method was successfully applied to enantioselective synthesis of (R)-precla
Dynamic kinetic resolution of racemic γ-aryl-δ-oxoesters. Enantioselective synthesis of 3-arylpiperidines
Amat, Mercedes,Canto, Margalida,Llor, Nuria,Escolano, Carmen,Molins, Elies,Espinosa, Enrique,Bosch, Joan
, p. 5343 - 5351 (2007/10/03)
Cyclodehydration of racemic γ-aryl-δ-oxoesters with (R)- or (S)-phenylglycinol stereoselectively affords bicyclic δ-lactams, in a process that involves a dynamic kinetic resolution. Subsequent reduction of these lactams leads to enantiopure 3-arylpiperidines. Starting from racemic aldehyde esters, this short sequence has been applied to the synthesis of (R)-3-phenylpiperidine and the antipsychotic drug (-)-3-PPP (an (S)-3-arylpiperidine), whereas starting from racemic ketone esters enantiopure cis-2-alkyl-3-arylpiperidines are prepared.
Dynamic kinetic resolution and desymmetrization of enantiotopic groups by cyclodehydration of racemic or prochiral δ-oxoesters with (R)-phenylglycinol: Enantioselective synthesis of piperidines
Amat, Mercedes,Canto, Margalida,Llor, Nuria,Ponzo, Viviana,Perez, Maria,Bosch, Joan
, p. 335 - 338 (2007/10/03)
Enantiotopic ester groups are desymmetrized in the cyclodehydration of prochiral δ-oxodiesters with (R)-phenylglycinol. This reaction can be extended to racemic δ-oxodiesters, which undergo a tandem dynamic kinetic resolution-diastereoselective differenti
Piperidine,3-phenyl-, (3R)- Synthetic route And Reaction conditions
- 56613-80-0
D-2-phenylglycinol
- 343947-52-4
methyl 5-oxo-4-phenylpentanoate
- 430461-56-6
(R)-3-phenyl piperidine
| Conditions | Yield |
|---|---|
- 430461-53-3
(3R)-1-[(1R)-2-hydroxy-1-phenylethyl]-3-phenylpiperidine
- 430461-56-6
(R)-3-phenyl piperidine
| Conditions | Yield |
|---|---|
| 75% |
- 430461-56-6
(R)-3-phenyl piperidine
| Conditions | Yield |
|---|---|
| 72% |
- 911465-34-4
((E)-(R)-2,4-Diphenyl-but-3-enyl)-carbamic acid benzyl ester
- 430461-56-6
(R)-3-phenyl piperidine
| Conditions | Yield |
|---|---|
Multi-step reaction with 3 steps 1: 76 percent / dimethylformamide / 50 °C 2: 85 percent / 2nd generation Grubbs catalyst / CH2Cl2 / 3.5 h / Heating 3: 72 percent / H2 / Pd/C / ethanol; ethyl acetate |
- 917810-87-8
Allyl-((E)-(R)-2,4-diphenyl-but-3-enyl)-carbamic acid benzyl ester
- 430461-56-6
(R)-3-phenyl piperidine
| Conditions | Yield |
|---|---|
Multi-step reaction with 2 steps 1: 85 percent / 2nd generation Grubbs catalyst / CH2Cl2 / 3.5 h / Heating 2: 72 percent / H2 / Pd/C / ethanol; ethyl acetate |
- 4663-33-6,62668-02-4,62839-70-7,116127-91-4,132014-29-0,136981-81-2,148616-45-9
1,3-diphenyl-3-hydroxypropene
- 430461-56-6
(R)-3-phenyl piperidine
| Conditions | Yield |
|---|---|
Multi-step reaction with 6 steps 1.1: pyridine; DMAP / tetrahydrofuran / 20 °C 2.1: 88 percent / aspartic acid-derived P-chirogenic diaminophosphine oxide; BSA; iPr2NEt / (η3-C3H5PdCl)2 / 3.5 h / 20 °C 3.1: SmI2 / methanol; tetrahydrofuran / 5 h / 0 - 20 °C 3.2: 87 percent / NEt3 / CH2Cl2 / 0.5 h / 20 °C 4.1: 76 percent / dimethylformamide / 50 °C 5.1: 85 percent / 2nd generation Grubbs catalyst / CH2Cl2 / 3.5 h / Heating 6.1: 72 percent / H2 / Pd/C / ethanol; ethyl acetate Withpyridine;
benzenesulfonamide;
dmap;
samarium diiodide;
aspartic acid-derived P-chirogenic diaminophosphine oxide;
hydrogen;
N-ethyl-N,N-diisopropylamine;tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride;
palladium on activated charcoal;
bis(η3-allyl-μ-chloropalladium(II));Intetrahydrofuran;
methanol;
ethanol;
dichloromethane;
ethyl acetate;
N,N-dimethyl-formamide; |
- 121440-71-9
ethyl (E)-1,3-diphenyl-2-propen-1-yl carbonate
- 430461-56-6
(R)-3-phenyl piperidine
| Conditions | Yield |
|---|---|
Multi-step reaction with 5 steps 1.1: 88 percent / aspartic acid-derived P-chirogenic diaminophosphine oxide; BSA; iPr2NEt / (η3-C3H5PdCl)2 / 3.5 h / 20 °C 2.1: SmI2 / methanol; tetrahydrofuran / 5 h / 0 - 20 °C 2.2: 87 percent / NEt3 / CH2Cl2 / 0.5 h / 20 °C 3.1: 76 percent / dimethylformamide / 50 °C 4.1: 85 percent / 2nd generation Grubbs catalyst / CH2Cl2 / 3.5 h / Heating 5.1: 72 percent / H2 / Pd/C / ethanol; ethyl acetate Withbenzenesulfonamide;
samarium diiodide;
aspartic acid-derived P-chirogenic diaminophosphine oxide;
hydrogen;
N-ethyl-N,N-diisopropylamine;tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride;
palladium on activated charcoal;
bis(η3-allyl-μ-chloropalladium(II));Intetrahydrofuran;
methanol;
ethanol;
dichloromethane;
ethyl acetate;
N,N-dimethyl-formamide; |
- 332-15-0
1-(2-phenylethynyl)piperidine
- 430461-56-6
(R)-3-phenyl piperidine
| Conditions | Yield |
|---|---|
Multi-step reaction with 4 steps 1.1: acetonitrile / 36 h / Heating 1.2: 45 percent / aqueous acetic acid / acetonitrile / 8 h / Heating 2.1: 49 percent / toluene / 24 h / Heating 3.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C 4.1: 75 percent / hydrogen / Pd(OH)2/C / ethyl acetate / 25 h / 25 °C |
- 122-78-1
phenylacetaldehyde
- 430461-56-6
(R)-3-phenyl piperidine
| Conditions | Yield |
|---|---|
Multi-step reaction with 5 steps 1.1: 78 percent / Na2CO3 / 3 h / 0 °C 2.1: acetonitrile / 36 h / Heating 2.2: 45 percent / aqueous acetic acid / acetonitrile / 8 h / Heating 3.1: 49 percent / toluene / 24 h / Heating 4.1: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C 5.1: 75 percent / hydrogen / Pd(OH)2/C / ethyl acetate / 25 h / 25 °C |
- 343947-52-4
methyl 5-oxo-4-phenylpentanoate
- 430461-56-6
(R)-3-phenyl piperidine
| Conditions | Yield |
|---|---|
Multi-step reaction with 3 steps 1: 49 percent / toluene / 24 h / Heating 2: 72 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C 3: 75 percent / hydrogen / Pd(OH)2/C / ethyl acetate / 25 h / 25 °C |
Piperidine,3-phenyl-, (3R)- Raw materials
- 56613-80-0
D-2-phenylglycinol
- 343947-52-4
methyl 5-oxo-4-phenylpentanoate
- 430461-53-3
(3R)-1-[(1R)-2-hydroxy-1-phenylethyl]-3-phenylpiperidine
- 911465-34-4
((E)-(R)-2,4-Diphenyl-but-3-enyl)-carbamic acid benzyl ester
- 917810-87-8
Allyl-((E)-(R)-2,4-diphenyl-but-3-enyl)-carbamic acid benzyl ester
Piperidine,3-phenyl-, (3R)- Target Products
- 957113-13-2
C37H48FN3O6
- 1367871-81-5
(R)-1-(3-phenylpiperidin1-yl)-3-(4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[4,3-c]pyridin-3-yl)propan-1-one
- 1367871-86-0
(R)-3-(4-(cyclohexyloxy)-1H-pyrazolo[4,3-c]pyridin-3-yl)-1-(3-phenylpiperidin-1-yl)propan-1-one
- 1446654-10-9
C31H34N2O3
- 1448667-86-4
(2'S,3R,4'R)-1,-(2,2-diphenylacetyl)-3-phenyl-[1,4'-bipiperidine]-2'-carboxylic acid
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Country :
China (Mainland)(35)
United Kingdom(1)
United States(1)
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