Pyrrolidine-1-carbonitrile → HCID 178454466, compound

HRID 609568Notes

Reaction equation

HRID 609568 reaction equation
[ClH:1].[CH2:2]([C:5]([NH:7][C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH2:11])=[O:6])[CH2:3][CH3:4].[N:15]1([C:20]#[N:21])[CH2:19][CH2:18][CH2:17][CH2:16]1>ClC1C=CC=CC=1.CN(C)C1C=CN=CC=1>[ClH:1].[CH2:2]([C:5]([NH:7][C:8]1[CH:9]=[C:10]([NH:11][C:20]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[NH:21])[CH:12]=[CH:13][CH:14]=1)=[O:6])[CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 73737Pyrrolidine-1-carbonitrileHCID 19599237N-(3-aminophenyl)butanamide hydrochloride

Product 1

HCID 178454466HCID 178454466, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7964ChlorobenzeneSolvent

Procedure

To a stirred suspension of the product of step (a), 2.3 g, 0.0135 moles. in 35 ml of chlorobenzene was added 4-dimethylaminopyridine. To this was added 1-pyrrolidinecarbonitrile, 1.2 ml, 0.006 moles, and the reaction was heated to reflux for 8 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 giving N-(3-(((propyl)carbonyl)amino)phenyl)-1-pyrrolidinecarboximidamide hydrochloride, 1.5 g, m.p. 207-208° C.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 8 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-f43a3bb6c05b44f6a33b0b98e187208e
Source dataset
uspto-grants-1999_12
Patent number
US05998399

Reaction notes

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