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

HRID 1988624Notes

Reaction equation

HRID 1988624 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-334db554ef7f48268502078ce2390bed
Source dataset
uspto-grants-2010_01
Patent number
US07642256B2

Reaction notes

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