Diisopropylethylamine → 1-[(5-Chloro-2-naphthyl)sulfonyl]-4-[4-fluoro-2-(trifluoromethyl)phenyl]piperazine

HRID 1868082Notes

Reaction equation

HRID 1868082 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[C:4]([C:14]([F:17])([F:16])[F:15])[CH:3]=1.[Cl:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH:21]=[CH:22][C:23]([S:29](Cl)(=[O:31])=[O:30])=[CH:24]2.C(N(C(C)C)CC)(C)C>ClCCl>[Cl:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH:21]=[CH:22][C:23]([S:29]([N:11]1[CH2:12][CH2:13][N:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=3[C:14]([F:16])([F:15])[F:17])[CH2:9][CH2:10]1)(=[O:30])=[O:31])=[CH:24]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27357775-Chloronaphthalene-2-sulphonyl chlorideHCID 579797591-(4-Fluoro-2-(trifluoromethyl)phenyl)piperazine

Product 1

HCID 685499391-[(5-Chloro-2-naphthyl)sulfonyl]-4-[4-fluoro-2-(trifluoromethyl)phenyl]piperazineYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfonylation of 1-(4-fluoro-2-(trifluoromethyl)phenyl)piperazine (193 mg, 3.888 mmol) with 5-chloronaphthalene-2-sulfonyl chloride (202.1 mg, 0.777 mmol) was carried out according to the representative sulfonation procedure described in Example 1 using anhydrous dichloromethane (3 mL) as solvent and diisopropylethylamine (0.7 mL, 3.887 mmol) as base. 1-[(5-chloro-2-naphthyl)sulfonyl]-4-[4-fluoro-2-(trifluoromethyl)phenyl]piperazine was obtained in 69% yield (256 mg) as white solid.

Sources & evidence

ORD record
ord-2105de867f564024ad60edbd77fcd79a
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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