Ethyl bromoacetate → [4-(4-Chloro-benzoyl)-piperidin-1-yl]-acetic acid ethyl ester

HRID 713431

반응식

HRID 713431 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[CH2:16]([O:18][C:19](=[O:22])[CH2:20]Br)[CH3:17].C(N(CC)CC)C>C(#N)C>[CH2:16]([O:18][C:19](=[O:22])[CH2:20][N:13]1[CH2:14][CH2:15][CH:10]([C:8](=[O:9])[C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:11][CH2:12]1)[CH3:17]

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 27771154-(4-Chlorobenzoyl)Piperidine

생성물 1

HCID 71226965[4-(4-Chloro-benzoyl)-piperidin-1-yl]-acetic acid ethyl ester수율 81.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
85 °C

실험 절차

To a suspension of (4-chloro-phenyl)-piperidin-4-yl-methanone (1.0 g, 3.8 mmol) and bromo-acetic acid ethyl ester (0.71 g, 4.2 mmol) in acetonitrile (10 mL) was added triethylamine (0.78 g, 7.7 mmol), the reaction mixture was stirred at 85° C. for 15 h. The reaction mixture was cooled to ambient temperature, the solvent was removed, the residue was redissolved in DCM (20 mL), washed with water (20 mL), the organic layers were then washed with brine (20 mL) and dried over Na2SO4. Purification by flash chromatography gave the title compound as a white solid (1.01 g, 3.10 mmol, 81% yield). MS (ESI) m/z 310.3 (M+H+); HPLC (Novapak 150×3.9 mm C-18 column: mobile phase: 35-90% acetonitrile/water with 0.1% TFA, at 2 mL/min over 2 min.) t 1.45 min.

후처리

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customthe solvent was removed
  3. dissolutionthe residue was redissolved in DCM (20 mL)
  4. washwashed with water (20 mL)
  5. washthe organic layers were then washed with brine (20 mL)
  6. dry with materialdried over Na2SO4
  7. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-b93deea389a9414db218e841e0a52304
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181266B2

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