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

HRID 1888435ノート

反応式

HRID 1888435 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-68c4936ffead43dbbc91c291c5dee62b
出典データセット
uspto-grants-2013_08
特許番号
US08501765B2

反応ノート

読み込み中…