2-Naphthalenesulfonyl chloride → HCID 68551185, compound

HRID 1868012Notes

Reaction equation

HRID 1868012 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[S:24](Cl)(=[O:26])=[O:25].S(Cl)(Cl)(=O)=O.C(N(C(C)C)CC)(C)C>ClCCl>[Cl:1][C:2]1[C:3]([N:8]2[CH2:9][CH2:10][N:11]([S:24]([C:15]3[CH:16]=[CH:17][C:18]4[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:14]=3)(=[O:26])=[O:25])[CH2:12][CH2:13]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 71252-Naphthalenesulfonyl chlorideHCID 24648Sulfuryl chlorideHCID 81531Diisopropylethylamine2×HCID 114129441-(3-Chloropyridin-2-yl)piperazine

Product 1

HCID 68551185HCID 68551185, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfonylation of 1-(3-chloropyridin-2-yl)piperazine (632 mg, 3.2 mmol) with naphthalene-2-sulfonyl chloride (725 mg, 3.2 mmol) was carried out according to a similar procedure described for example 2A (except that the sulfonyl chloride was added before the diisopropylethylamine) using anhydrous dichloromethane (10 mL) as solvent and diisopropylethylamine (1.4 mL, 8.0 mmol) as base. 1-(3-chloropyridin-2-yl)-4-(2-naphthylsulfonyl)piperazine was obtained in 17.0% yield (210.2 mg) as white solid.

Sources & evidence

ORD record
ord-11848e2897564bbbb05b3b2802b9f0cc
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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