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

HRID 1616342Notes

Reaction equation

HRID 1616342 reaction equation
[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

Participants

6

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 4209294-Bromopiperidine

Product 1

HCID 113590324-Bromo-1-tosylpiperidine

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-b18ca18d8e344a2d89ea0b4148b50060
Source dataset
uspto-grants-2014_07
Patent number
US08765788B2

Reaction notes

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