p-Bromobenzenesulfonyl chloride → 1-(4-Bromophenylsulphonyl)-4-[4-(4-pyridyl)-1-piperidylmethyl]piperidine

HRID 1249722Notes

Reaction equation

HRID 1249722 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.Cl.Cl.Cl.[N:15]1[CH:20]=[CH:19][C:18]([CH:21]2[CH2:26][CH2:25][N:24]([CH2:27][CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[CH2:23][CH2:22]2)=[CH:17][CH:16]=1.C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:31]2[CH2:32][CH2:33][CH:28]([CH2:27][N:24]3[CH2:23][CH2:22][CH:21]([C:18]4[CH:19]=[CH:20][N:15]=[CH:16][CH:17]=4)[CH2:26][CH2:25]3)[CH2:29][CH2:30]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 183289274-[4-(4-Pyridyl)-1-piperidylmethyl]piperidine trihydrochloride

Product 1

HCID 183288991-(4-Bromophenylsulphonyl)-4-[4-(4-pyridyl)-1-piperidylmethyl]piperidineYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 4-bromophenylsulphonyl chloride (411 mg) in methylene chloride (4 ml) was added dropwise over 15 minutes to a mixture of 4-[4-(4-pyridyl)-1-piperidylmethyl]piperidine trihydrochloride (545 mg) and triethylamine (1.07 ml) in dichloromethane (10 ml) at 0° C. The solution was stirred at ambient temperature for 18 hours. The solution was diluted with dichloromethane and washed with water, dried (Na2SO4) and evaporated. The residue was purified by chromatography eluting with 4% methanol in dichloromethane. Recrystallisation from ethyl acetate/hexane gave, as a solid 1-(4-bromophenylsulphonyl)-4-[4-(4-pyridyl)-1-piperidylmethyl]piperidine (410 mg), mp 163-164° C.

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe residue was purified by chromatography
  5. washeluting with 4% methanol in dichloromethane
  6. customRecrystallisation from ethyl acetate/hexane

Sources & evidence

ORD record
ord-4988eb35dc89480e9977b477de5a8220
Source dataset
uspto-grants-2002_01
Patent number
US06335341B1

Reaction notes

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