Chloroacetamide → 2-[7-(3-Fluoro-benzyloxy)-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl]-acetamide

HRID 346452

반응식

HRID 346452 반응식
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[CH2:6][O:7][C:8]1[CH:18]=[CH:17][C:11]2[CH2:12][CH2:13][NH:14][CH2:15][CH2:16][C:10]=2[CH:9]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:29][C:30]([NH2:32])=[O:31]>CC(C)=O>[F:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[CH2:6][O:7][C:8]1[CH:18]=[CH:17][C:11]2[CH2:12][CH2:13][N:14]([CH2:29][C:30]([NH2:32])=[O:31])[CH2:15][CH2:16][C:10]=2[CH:9]=1

참가 물질

5

반응물 3

HCID 6580ChloroacetamideHCID 11430Potassium CarbonateHCID 210801847-(3-fluoro-benzyloxy)-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride

생성물 1

HCID 114616002-[7-(3-Fluoro-benzyloxy)-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl]-acetamide수율 51%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A solution of 70 mg (0.23 mmol) of 7-(3-fluoro-benzyloxy)-2,3,4,5-tetrahydro-1H-benzo[d]azepine hydrochloride [Example 1c)] in 1 ml of acetone was successively treated with 69 mg (0.5 mmol) of potassium carbonate and 24 mg (0.25 mmol) of 2-chloroacetamide. The reaction mixture was heated to reflux during 18 h. For the working-up, 1 g of silica gel was added to the cooled reaction mixture, which was then evaporated under reduced pressure. For purification, the crude material obtained was chromatographed on silica gel using a 95:5:0.1-mixture of dichloromethane, methanol and ammonium hydroxide as the eluent. There were obtained 38 mg (51% of theory) of 2-[7-(3-fluoro-benzyloxy)-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl]-acetamide as a white solid; MS: m/e 329 (M+H)+.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux during 18 h
  3. addition1 g of silica gel was added to the cooled reaction mixture, which
  4. customwas then evaporated under reduced pressure
  5. customFor purification
  6. customthe crude material obtained
  7. customwas chromatographed on silica gel using a 95:5

출처 및 근거

ORD 기록
ord-108d1cfb19e5400cb33f1a87da97a5a0
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173023B2

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