1-Benzylpyrrolidine-3-carbonitrile

Base Information

• Chemical Name: 1-Benzylpyrrolidine-3-carbonitrile
• CAS No.: 10603-52-8
• Molecular Formula: C12H14N2
• Molecular Weight: 186.257
• Hs Code.: 2933990090
• European Community (EC) Number: 676-149-6
• ChEMBL ID: CHEMBL4549555
• DSSTox Substance ID: DTXSID60405451
• Nikkaji Number: J2.367.992B
• Mol file: 10603-52-8.mol

Synonyms:1-benzylpyrrolidine-3-carbonitrile;10603-52-8;1-Benzyl-pyrrolidine-3-carbonitrile;1-benzyl-3-cyano-pyrrolidine;1-Benzyl-3-cyanopyrrolidine;3-pyrrolidinecarbonitrile, 1-(phenylmethyl)-;MFCD05662780;SCHEMBL607250;CHEMBL4549555;AMY2549;DTXSID60405451;RYCQUUNQHVAFSM-UHFFFAOYSA-N;1-benzyl-3-pyrrolidinecarbonitrile;AKOS009459637;AB92139;CS-W016891;SB44986;SB44989;(r,s)-1-benzylpyrrolidine-3-carbonitrile;AS-36343;SY011027;FT-0653307;EN300-138976;1-Benzyl-pyrrolidine-3-carbonitrile, AldrichCPR;2,4-DINITROTOLUENE-5-SULFONICACIDSODIUMSALT;J-001532;Z415654888

Chemical Property of 1-Benzylpyrrolidine-3-carbonitrile

Chemical Property:

• Vapor Pressure: 0.0005mmHg at 25°C
• Refractive Index: 1.572
• Boiling Point: 313.3 °C at 760 mmHg
• PKA: 7.26±0.40(Predicted)
• Flash Point: 132.8 °C
• PSA: 27.03000
• Density: 1.08 g/cm³
• LogP: 1.96998
• Storage Temp.: Room temperature.
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 186.115698455
• Heavy Atom Count: 14
• Complexity: 222

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-Benzylpyrrolidine-3-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CC1C#N)CC2=CC=CC=C2

Technology Process of 1-Benzylpyrrolidine-3-carbonitrile

There total 9 articles about 1-Benzylpyrrolidine-3-carbonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

zinc(II) cyanide (557-21-1) + 1-benzyl-3-chloropyrrolidine (10603-48-2,204973-04-6) → 1-benzyl-pyrrolidine-3-carbonitrile (10603-52-8)

Guidance literature:

With dmap; nickel(II) chloride hexahydrate; tetrabutyl-ammonium chloride; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; zinc; In acetonitrile; at 100 ℃; for 8h; Inert atmosphere; Glovebox;

Reference yield: 83.0%

1-benzyl-3-chloropyrrolidine (10603-48-2,204973-04-6) + dicyanozinc (557-21-1) → 1-benzyl-pyrrolidine-3-carbonitrile (10603-52-8)

Guidance literature:

With dmap; nickel(II) chloride hexahydrate; tetrabutyl-ammonium chloride; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; zinc; In acetonitrile; at 100 ℃; for 8h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b03539

Reference yield: 70.0%

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (93102-05-7) + acrylonitrile (107-13-1,25014-41-9) → 1-benzyl-pyrrolidine-3-carbonitrile (10603-52-8)

Guidance literature:

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine; acrylonitrile; With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃;

With sodium hydrogencarbonate; In dichloromethane; water;

upstream raw materials:

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine

acrylonitrile

sodium cyanide

(3R)-1-benzyl-3-methanesulfonyloxy pyrrolidine

Downstream raw materials:

1-benzyl-3-carboethoxypyrrolidine

1-benzyl-3-(quinazolin-4-yl)pyrrolidine-3-carbonitrile

3-ethoxycarbonyl-pyrrolidine

(+/-)-3-(1-benzylpyrrolidin-3-yl)-5-methyl-2H-isoquinolin-1-one

Refernces

• 1、 Xu, Jianyu,Twitty, J. Cameron,Watson, Mary P.. "Nickel-Catalyzed Deaminative Cyanation: Nitriles and One-Carbon Homologation from Alkyl Amines". . p. 6242 - 6245. Retrieved 2021.
• 2、 Xia, Aiyou,Xie, Xin,Chen, Haoyi,Zhao, Jidong,Zhang, Chunli,Liu, Yuanhong. "Nickel-Catalyzed Cyanation of Unactivated Alkyl Chlorides or Bromides with Zn(CN)2". supporting information. p. 7735 - 7739. Retrieved 2019/01/03.