Pyrrolidine → 1-[2-(4-Bromophenyl)propanoyl]pyrrolidine

HRID 230621Notes

Reaction equation

HRID 230621 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:12])[C:9]([N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 682631,1'-CarbonyldiimidazoleHCID 5214412-(4-Bromophenyl)propanoic acid

Product 1

HCID 577628121-[2-(4-Bromophenyl)propanoyl]pyrrolidineYield 71.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(4-bromophenyl)propanoic acid (215 mg, 0.94 mmol) in dichloromethane (4 ml) was treated in one portion with solid 1,1′-carbonyldiimidazole (152 g, 0.94 mmol). This mixture was allowed to stir at room temperature for 15 minutes. Pyrrolidine (67 mg, 0.94 mmol) was then added and the stirring continued for 1 hour at room temperature. Most of the solvent was removed under reduced pressure and the residue added to a 5 g pre-packed silica column and eluted from 0-50% ethyl acetate in petroleum ether to give the title compound as a colourless solid (189 mg, 71%).

Workup

  1. waitthe stirring continued for 1 hour at room temperature
  2. customMost of the solvent was removed under reduced pressure
  3. additionthe residue added to a 5 g pre-packed silica column
  4. washeluted from 0-50% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-0b7edc98aebd474d9c76da73d84c8654
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Reaction notes

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