Water → trans-1-Benzenesulfonyl-3-(3-chloro-phenyl)-4-phenyl-piperidine

HRID 560121Notes

Reaction equation

HRID 560121 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]2[C@H:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][CH2:11][NH:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>C(Cl)Cl>[C:20]1([S:26]([N:10]2[CH2:11][CH2:12][C@@H:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C@H:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[CH2:9]2)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 14913322Rac-trans-3-(m-chlorophenyl)-4-phenylpiperidine

Product 1

HCID 67000691trans-1-Benzenesulfonyl-3-(3-chloro-phenyl)-4-phenyl-piperidineYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the hydrochloride salt of rac-trans-3-(m-chlorophenyl)-4-phenylpiperidine (CAS Reg. No.: [134823-41-9]) (500 mg) in methylene chloride (10 mL) triethylamine (677 μL) and benzenesulfonyl chloride (229 μL) were added. The reaction mixture was stirred at room temperature for 4 h, water was added, the phases were separated, and the inorganic one was extracted with ethyl acetate (×3). The organic layers were combined, washed with brine, dried (Na2SO4) and concentrated in vacuo. Column chromatography (SiO2, n-heptane/ethyl acetate 3:1) yielded trans-1-benzenesulfonyl-3-(3-chloro-phenyl)-4-phenyl-piperidine (0.66 g, 98%) as a white foam, MS: 411 (M, 1 Cl).

Workup

  1. customthe phases were separated
  2. extractionthe inorganic one was extracted with ethyl acetate (×3)
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-01cd4544dcad4154a846cdfa805b443b
Source dataset
uspto-grants-2011_11
Patent number
US08063088B2

Reaction notes

Loading…