Pyrrolidine-1-carbonitrile → HCID 178419712, compound

HRID 609569Notes

Reaction equation

HRID 609569 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1.[BrH:18].C(N(CC)C1C=CC=CC=1)C.[N:30]1([C:35]#[N:36])[CH2:34][CH2:33][CH2:32][CH2:31]1>ClC1C=CC=CC=1.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[BrH:18].[N:12]1([C:10]([CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:35]([N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[NH:36])=[CH:3][CH:4]=2)=[O:11])[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1

Participants

7

Reactant 3

HCID 73737Pyrrolidine-1-carbonitrileHCID 195992744-(3-(4-Aminophenyl)propionyl)morpholineHCID 19599275N,N-diethylaniline hydrobromide

Product 1

HCID 178419712HCID 178419712, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7964ChlorobenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of step (b) (2.22 g, 0.00948 moles) was dissolved in 15 ml chlorobenzene. N,N-diethylaniline hydrobromide (2.18 g, 0.00948 moles) was added followed by 1-pyrrolidinecarbonitrile (1.37 g, 0.01422 moles). A catalytic amount of 4-dimethylaminopyridine was added and the reaction heated to reflux for 6 hours. The reaction was then cooled to room temperature and diluted with 100 ml ethyl acetate. A sticky oil precipitated from solution and was stirred for 24 hours. The resulting solids were filtered and recrystallized from hot isopropanol to give the N-(4(2-((4-morpholinyl)carbonyl)ethyl)phenyl)-1-pyrrolidinecarboximidamide hydrobromide, M.P. 207-209° C.

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 6 hours
  3. customA sticky oil precipitated from solution
  4. filtrationThe resulting solids were filtered
  5. customrecrystallized from hot isopropanol

Sources & evidence

ORD record
ord-dd7903ff75864863a37c62eaa4813439
Source dataset
uspto-grants-1999_12
Patent number
US05998399

Reaction notes

Loading…