p-Bromobenzenesulfonyl chloride → Piperidine, 1-((p-bromophenyl)sulfonyl)-

HRID 2239401Notes

Reaction equation

HRID 2239401 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8082Piperidine

Product 1

HCID 95051Piperidine, 1-((p-bromophenyl)sulfonyl)-Yield 27.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to general procedure C, 4-Bromobenzene sulfonyl chloride (0.40 g, 1.56 mmol) and piperidine (0.38 mL, 3.90 mmol) were stirred together in dry dichloromethane (5 mL) for 16 hours. 1-[(4-bromophenyl)sulfonyl]piperidine (0.13 g) was provided after purification. HRMS: calcd for C11H14BrNO2S+H+, 304.00014; found (ESI, [M+H]+), 304.0009. HPLC purity 99.2% at 210-370 nm, 9.8 min.; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min., 85/15-5/95 (ammonium formate buffer pH=3.5/ACN+MeOH) for 10 min., hold 4 min.

Sources & evidence

ORD record
ord-be504f9714904cefa0536b48c0c688df
Source dataset
uspto-grants-2010_05
Patent number
US07723332B2

Reaction notes

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