4-Toluenesulfonyl chloride → 4-Bromo-1-tosylpiperidine

HRID 1616342ノート

反応式

HRID 1616342 の反応式
[Br:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[S:8](Cl)([C:11]1[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=1)(=[O:10])=[O:9]>N1C=CC=CC=1.ClCCl.Cl>[Br:1][CH:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:4][CH2:3]1

参加物

6

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 4209294-Bromopiperidine

生成物 1

HCID 113590324-Bromo-1-tosylpiperidine

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

実験手順

4-Bromopiperidine (5.75 g, 23.5 mmol) was dissolved in pyridine (50 mL) and treated with tosyl chloride (5.8 g, 30.5 mmol). The reaction mixture was stirred for 12 h at r.t. and then diluted with dichloromethane (150 mL) and HCl (1 M aqueous solution, 50 mL). The organic layer was washed with brine (80 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (40% EtOAc/hexane) to give 4-bromo-1-tosylpiperidine as a white solid: 1H NMR (400 MHz, CDCl3) δ 7.66 (d, J=8.2 Hz, 2H), 7.34 (d, J=8.2 Hz, 2H), 4.27-4.24 (m, 1H), 3.20-3.17 (m, 2H), 3.13-3.11 (m, 2H), 2.46 (s, 3H), 2.23-2.17 (m, 2H), 2.08-2.05 (m, 2H); MS (ESI) 318.0 (M+H)+.

後処理

  1. washThe organic layer was washed with brine (80 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (40% EtOAc/hexane)

出典と根拠

ORDレコード
ord-b18ca18d8e344a2d89ea0b4148b50060
出典データセット
uspto-grants-2014_07
特許番号
US08765788B2

反応ノート

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