4-Methoxybenzenesulfonyl chloride → HCID 44248580, compound

HRID 1868152Notes

Reaction equation

HRID 1868152 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH:10]([CH3:14])[CH2:9]2)=[C:4]([C:15]([F:18])([F:17])[F:16])[CH:3]=1.CCN(C(C)C)C(C)C.[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:36]([C:33]3[CH:32]=[CH:31][C:30]([O:29][CH3:28])=[CH:35][CH:34]=3)(=[O:38])=[O:37])[C@H:10]([CH3:14])[CH2:9]2)=[C:4]([C:15]([F:17])([F:16])[F:18])[CH:3]=1

Participants

5

Reactant 3

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 68554323Piperazine, 1-[4-fluoro-2-(trifluoromethyl)phenyl]-3-methyl-

Product 1

HCID 44248580HCID 44248580, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To solution of 1-(4-Fluoro-2-trifluoromethyl-phenyl)-3-methyl-piperazine (200 mg, 0.76 mmol) and DIPEA (0.33 mL, 1.90 mmol) in DCM (8.0 mL) was added 4-Methoxybenzenesulfonyl chloride. The reaction was allowed to stir over a 12-16 hr period, after which it was judged complete by TLC. The reaction mixture was concentrated in-vacuo, and the resultant crude oil was purified via normal phase SiO2 column chromatography using a 2%-10% EtOAc/Hex solvent gradient. The desired product, was isolated in >95% purity. HRMS: calcd for C19H20F4N2O3S+H+, 433.12035. found ([M+H]1+), 433.12037.

Workup

  1. concentrationThe reaction mixture was concentrated in-vacuo
  2. customthe resultant crude oil was purified via normal phase SiO2 column chromatography

Sources & evidence

ORD record
ord-1a113cc40bcb40c1b4df6315cf790082
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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