Triethylamine → 4-Bromo-N-(cyclopropylmethyl)benzamide

HRID 1272702Notes

Reaction equation

HRID 1272702 reaction equation
[CH:1]1([CH2:4][NH2:5])[CH2:3][CH2:2]1.C(N(CC)CC)C.[Br:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>C1COCC1>[Br:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)=[O:19])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 685154-Bromobenzoyl chlorideHCID 75646Cyclopropanemethanamine

Product 1

HCID 184578074-Bromo-N-(cyclopropylmethyl)benzamideYield 74.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cyclopropylmethylamine (1.62 g, 22.8 mmol) and triethylamine (3 ml) were dissolved in THF (40 ml) and 4-bromobenzoylchloride (5 g, 22.8 mmol) added over 5 min at 0° C. The reaction was stirred at room temperature for 16 h, reduced to dryness under vacuum and the residue partitioned between DCM (75 ml) and water (75 ml). The aqueous was extracted with DCM (2×50 ml). The combined organic phases were washed with brine, dried (magnesium sulphate) and the solvent evaporated under vacuum. The residue was purified by flash column chromatography on silica eluting with cyclohexane/ethyl acetate (8:2). The solvent was evaporated from the product fractions under vacuum to give 4-bromo-N-cyclopropylmethylbenzamide (4.3 g, 74%). LCMS: retention time 3.00 min, MH+255.

Workup

  1. customthe residue partitioned between DCM (75 ml) and water (75 ml)
  2. extractionThe aqueous was extracted with DCM (2×50 ml)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried (magnesium sulphate)
  5. customthe solvent evaporated under vacuum
  6. customThe residue was purified by flash column chromatography on silica eluting with cyclohexane/ethyl acetate (8:2)
  7. customThe solvent was evaporated from the product fractions under vacuum

Sources & evidence

ORD record
ord-9d121f87227d4849ae4bb27667b7d37e
Source dataset
uspto-grants-2007_04
Patent number
US07208629B2

Reaction notes

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