2-Naphthalenesulfonyl chloride → 1-(2-Ethylphenyl)-4-(2-naphthylsulfonyl)piperazine

HRID 1868019Notes

Reaction equation

HRID 1868019 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)[CH3:2].[CH:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1[S:25](Cl)(=[O:27])=[O:26].C(N(C(C)C)CC)(C)C>ClCCl>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([S:25]([C:16]2[CH:17]=[CH:18][C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:15]=2)(=[O:27])=[O:26])[CH2:13][CH2:14]1)[CH3:2]

Participants

5

Reactant 3

HCID 71252-Naphthalenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 27364601-(2-Ethylphenyl)piperazine

Product 1

HCID 685521321-(2-Ethylphenyl)-4-(2-naphthylsulfonyl)piperazineYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfonylation of 1-(2-ethylphenyl)piperazine (293 mg, 1.54 mmol) with naphthalene-2-sulfonyl chloride (350 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 (0.670 mL, 3.85 mmol) as base. 1-(2-ethylphenyl)-4-(2-naphthylsulfonyl)piperazine was obtained in 99% yield (579 mg) as white solid.

Sources & evidence

ORD record
ord-e03cbfb61abb4f9083568e8025aa64ce
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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