2-Naphthalenesulfonyl chloride → 1-[4-Fluoro-2-(methylsulfonyl)phenyl]-4-(2-naphthylsulfonyl)piperazine

HRID 1868020Notes

Reaction equation

HRID 1868020 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]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:3]=1.[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[S:28](Cl)(=[O:30])=[O:29].C(N(C(C)C)CC)(C)C>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([S:28]([C:19]3[CH:20]=[CH:21][C:22]4[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:18]=3)(=[O:30])=[O:29])[CH2:12][CH2:13]2)=[C:4]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:3]=1

Participants

5

Reactant 3

HCID 71252-Naphthalenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 27827311-[4-Fluoro-2-(methylsulfonyl)phenyl]piperazine

Product 1

HCID 685540081-[4-Fluoro-2-(methylsulfonyl)phenyl]-4-(2-naphthylsulfonyl)piperazineYield 61.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfonylation of 1-(4-fluoro-2-(methylsulfonyl)phenyl)piperazine (316.6 mg, 1.23 mmol) with naphthalene-2-sulfonyl chloride (278 mg, 1.54 mmol) was carried out according to a similar procedure described for example 3A using anhydrous dichloromethane (5 mL) as solvent and diisopropylethylamine (0.256 mL, 1.47 mmol) as base. 1-[4-fluoro-2-(methylsulfonyl)phenyl]-4-(2-naphthylsulfonyl)piperazine was obtained in 61.8% yield (340 mg) as white solid.

Sources & evidence

ORD record
ord-81984522c38c48fbb7e3fe6c9b967044
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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