Pyrrolidine-1-carbonitrile → HCID 178479312, compound

HRID 609565Notes

Reaction equation

HRID 609565 reaction equation
[ClH:1].[C:2]1([CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([C:15]2[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=2)[NH2:18])=[O:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:22]1([C:27]#[N:28])[CH2:26][CH2:25][CH2:24][CH2:23]1>ClC1C=CC=CC=1.CN(C)C1C=CN=CC=1>[ClH:1].[C:2]1([CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([C:15]2[CH:16]=[C:17]([NH:18][C:27]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[NH:28])[CH:19]=[CH:20][CH:21]=2)=[O:14])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 73737Pyrrolidine-1-carbonitrileHCID 193536943-(((4-Phenylbutyl)amino)carbonyl)aniline hydrochloride

Product 1

HCID 178479312HCID 178479312, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7964ChlorobenzeneSolvent

Procedure

To a stirred suspension of the product of step (a), 2.0 g, 0.006 moles, in 35 ml of chlorobenzene was added 4-dimethylaminopyridine. To this was added 1-pyrrolidinecarbonitrile, 1.5 ml; 0.008 moles, and the reaction was heated to reflux for 4 hours. The reaction cooled to room temperature and the solvent was decanted. To the residue was added 25 ml of isopropanol and 150 ml of ethyl acetate. A solid crystallized and was collected by filtration. The above solid was then dried at 80° C. for 24 hours to give N-[3-(((4-phenylbutyl)amino)carbonyl)phenyl]-1-pyrrolidinecarboximidamide hydrochloride, 2.3 g, m.p. 197-198° C.

Workup

  1. temperature0.008 moles, and the reaction was heated
  2. temperatureto reflux for 4 hours
  3. customthe solvent was decanted
  4. additionTo the residue was added 25 ml of isopropanol and 150 ml of ethyl acetate
  5. customA solid crystallized
  6. filtrationwas collected by filtration
  7. customThe above solid was then dried at 80° C. for 24 hours

Sources & evidence

ORD record
ord-6497bc1083d54343bd4263b16d49df8a
Source dataset
uspto-grants-1999_12
Patent number
US05998399

Reaction notes

Loading…