Triethylamine → N-[(4-bromophenyl)methyl]-1-pyrrolidinecarboxamide

HRID 230635

Reaction equation

HRID 230635 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][N:7]=[C:8]=[O:9])=[CH:4][CH:3]=1.[CH2:12]([N:14](CC)[CH2:15][CH3:16])[CH3:13].N1CCCC1>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([N:14]2[CH2:15][CH2:16][CH2:13][CH2:12]2)=[O:9])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 43746174-Bromobenzyl isocyanate

Product 1

HCID 57762826N-[(4-bromophenyl)methyl]-1-pyrrolidinecarboxamideYield 99.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-bromobenzylisocyanate (408 mg, 1.92 mmol) in acetonitrile (15 ml) was treated with triethylamine (390 mg, 3.86 mmol) followed by pyrrolidine (137 mg, 1.93 mmol) at room temperature with stirring under argon. The reaction was stirred at 20° C. for 30 minutes and then partitioned between ethyl acetate (10 ml) and water (20 ml). The organic layer was dried over sodium sulphate and evaporated under reduced pressure to give the title compound as a colourless solid (542 mg, 99%).

Workup

  1. stirringThe reaction was stirred at 20° C. for 30 minutes
  2. custompartitioned between ethyl acetate (10 ml) and water (20 ml)
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f443a1ad5c914714b68e4eed5bc82f15
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Linked notes

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