Piperidine → 1-(3-Bromo-5-methoxybenzyl)piperidine

HRID 1505898ノート

反応式

HRID 1505898 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH:5]=O.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.[BH4-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH2:5][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

参加物

5

反応物 3

HCID 8082PiperidineHCID 4311764Sodium borohydrideHCID 106086983-Bromo-5-methoxybenzaldehyde

生成物 1

HCID 582665711-(3-Bromo-5-methoxybenzyl)piperidine収率 69%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a pre-stirred solution of 3-bromo-5-methoxybenzaldehyde (0.56 g, 2.61 mmol) and piperidine (0.29 mL, 3.93 mmol) in DCM (10 mL) at 0° C. was added sodium borohydride (197 mg, 5.22 mmol) in portions. The reaction mixture was allowed to warm to ambient temperature and stirred for an additional 2 h. The reaction was quenched by the addition of water (30 mL) and extracted into ethyl acetate (75 mL) then washed with water (50 mL) then the organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford the title compound as a colourless oil (510 mg, 69%) that was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz): 7.08-7.06 (m, 1H), 6.94-6.91 (m, 1H), 6.83-6.80 (s, 1H), 3.79 (s, 3H), 3.39 (s, 2H), 2.40-2.30 (s, 4H), 1.61-1.51 (m, 4H), 1.47-1.38 (m, 2H).

後処理

  1. customThe reaction was quenched by the addition of water (30 mL)
  2. extractionextracted into ethyl acetate (75 mL)
  3. washthen washed with water (50 mL)
  4. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

出典と根拠

ORDレコード
ord-126c368ee5964b87a7c8fdb8caf5259c
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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