Pyrrolidine-1-carbonitrile → HCID 178479317, compound

HRID 609563Notes

Reaction equation

HRID 609563 reaction equation
[ClH:1].[C:2]1([CH2:8][CH2:9][C:10]([NH:12][C:13]2[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=2)[NH2:16])=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:20]1([C:25]#[N:26])[CH2:24][CH2:23][CH2:22][CH2:21]1>ClC1C=CC=CC=1.CN(C)C1C=CN=CC=1>[ClH:1].[C:2]1([CH2:8][CH2:9][C:10]([NH:12][C:13]2[CH:14]=[C:15]([NH:16][C:25]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[NH:26])[CH:17]=[CH:18][CH:19]=2)=[O:11])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 73737Pyrrolidine-1-carbonitrileHCID 195992863-(((2-Phenylethyl)carbonyl)amino)aniline hydrochloride

Product 1

HCID 178479317HCID 178479317, 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, 1.2 ml, 0.06 moles, and the reaction was heated to reflux for 4 hours. The reaction was cooled to room temperature and the solvent 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 60° C. for 24 hours giving 700 mg of N-(3-(((2-phenylethyl)carbonyl)amino)phenyl)-1-pyrrolidinecarboximidamide hydrochloride, m.p. 220-221° C.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 4 hours
  3. customthe solvent 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 60° C. for 24 hours

Sources & evidence

ORD record
ord-06238005818a4d3884b42060c67a7502
Source dataset
uspto-grants-1999_12
Patent number
US05998399

Reaction notes

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