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

HRID 1616342노트

반응식

HRID 1616342 반응식
[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

참가 물질

6

반응물 2

HCID 73974-Toluenesulfonyl chlorideHCID 4209294-Bromopiperidine

생성물 1

HCID 113590324-Bromo-1-tosylpiperidine

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 1049Pyridine용매HCID 6344Dichloromethane용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-b18ca18d8e344a2d89ea0b4148b50060
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765788B2

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