Triethylamine → (4-Bromophenyl)(pyrrolidin-1-yl)methanone

HRID 1673152Notes

Reaction equation

HRID 1673152 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.C(N(CC)CC)C>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 685154-Bromobenzoyl chloride

Product 1

HCID 819718(4-Bromophenyl)(pyrrolidin-1-yl)methanoneYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-bromobenzoyl chloride (3 g, 13.7 mmol)) in dichloromethane (25 mL) was cooled to 0° C. and treated with pyrrolidine (2.5 mL, 30.3 mmol) and triethylamine (2 mL, 14.4 mmol). The mixture was warmed to ambient temperature over 3 hours and concentrated. The residue was purified by flash chromatography on silica gel using 10-60% hexane/ethyl acetate to provide the title compound (3.1 g, 89%). MS (ESI) m/e 256 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash chromatography on silica gel using 10-60% hexane/ethyl acetate

Sources & evidence

ORD record
ord-a8879595b171487bbec3b8d006bcad36
Source dataset
uspto-grants-2011_08
Patent number
US07999117B2

Reaction notes

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