Propylamine → 3-bromo-N-propylbenzamide

HRID 30582

반응식

HRID 30582 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 31186553-bromo-N-propylbenzamide수율 67%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-5 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-fb1e271f2d5641358ec23bf5560de3df
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423158B2

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