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

HRID 1505895ノート

反応式

HRID 1505895 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 534861121-(4-Bromo-2-fluorobenzyl)piperidine収率 106.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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. 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).

後処理

  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

出典と根拠

ORDレコード
ord-9977893c039d4400bf6dd7d83a221e3a
出典データセット
uspto-grants-2015_12
特許番号
US09216980B2

反応ノート

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