Piperidine → 1-(4-Bromo-2-fluorobenzyl)piperidine

HRID 1888432노트

반응식

HRID 1888432 반응식
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([F:10])[CH:3]=1.[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:4]([F:10])[CH:3]=1

참가 물질

5

반응물 3

HCID 8082PiperidineHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 534861121-(4-Bromo-2-fluorobenzyl)piperidine수율 106.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a pre-stirred solution of 4-bromo-2-fluorobenzaldehyde (1.82 g, 9.0 mmol) and piperidine (0.97 mL, 9.9 mmol) in DCM (40 mL) at 0° C. was added sodium triacetoxyborohydride (2.85 g, 13.4 mmol) in portions. The reaction mixture was allowed to warm to ambient temperature and stirred for an additional 14 h. The reaction was quenched by the addition of water (30 mL) and extracted with ethyl acetate (75 mL). The organic phase was separated, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford the title compound as a colourless oil (2.6 g, 84%) that was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz): 7.33-7.17 (m, 3H), 3.49 (d, J=1.6 Hz, 2H), 2.43-2.33 (m, 4H), 1.61-1.53 (m, 4H), 1.46-1.38 (m, 2H).

후처리

  1. customThe reaction was quenched by the addition of water (30 mL)
  2. extractionextracted with ethyl acetate (75 mL)
  3. customThe organic phase was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-ebf12c8ffa2a489287f1a199f755243f
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501765B2

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