Propylamine → 3-bromo-N-propylbenzamide

HRID 30582

Reaction equation

HRID 30582 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].C(N(CC)CC)C.[Br:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16](Cl)=[O:17].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([NH:4][CH2:1][CH2:2][CH3:3])=[O:17]

Participants

6

Reactant 4

HCID 7852PropylamineHCID 8471TriethylamineHCID 74377Benzoyl chloride, 3-bromo-HCID 516892Sodium Bicarbonate

Product 1

HCID 31186553-bromo-N-propylbenzamideYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

A mixture of N-propyl amine (0.33 mL, 4.1 mmol) and triethylamine (0.83 mL, 5.8 mmol) in methylene chloride was cooled to −5° C., treated with 3-bromobenzoyl chloride (1 g, 4.5 mmol), warmed to room temperature, stirred at room temperature for 1 h, poured into aqueous sodium bicarbonate and extracted with methylene chloride. The extracts were combined, washed sequentially with water and brine, dried over magnesium sulfate and concentrated under reduced pressure. The resultant residue was purified by flash chromatography on silica gel, 2:1 hexane/ethyl acetate as eluent, to give 3-bromo-N-propyl-benzamide as a white solid, 0.74 g (67% yield); 1H NMR (DMSO-d6) δ 0.8 (t, 3H); 1.5 (m, 2H); 3.2 (t, 2H); 7.4 (t, 1H); 7.6 (d, 1H), 7.8 (d, 1H); 7.9 (s, 1H); 8.5 (b, 1H); MS [(+)ESI] m/z 242[M−H]+.

Workup

  1. temperaturewarmed to room temperature
  2. extractionextracted with methylene chloride
  3. washwashed sequentially with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant residue was purified by flash chromatography on silica gel, 2:1 hexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-fb1e271f2d5641358ec23bf5560de3df
Source dataset
uspto-grants-2008_09
Patent number
US07423158B2

Linked notes

Loading…