3-(Bromomethyl)benzene-1-sulfonyl chloride → HCID 23447331, compound

HRID 2186189Notes

Reaction equation

HRID 2186189 reaction equation
Cl.[C:2]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][NH:12][CH2:11][C:10]2=[O:15])=[CH:6][CH:5]=1)#[N:3].[Br:18][CH2:19][C:20]1[CH:21]=[C:22]([S:26](Cl)(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1>>[Br:18][CH2:19][C:20]1[CH:21]=[C:22]([S:26]([N:12]2[CH2:13][CH2:14][N:9]([CH2:8][C:7]3[CH:6]=[CH:5][C:4]([C:2]#[N:3])=[CH:17][CH:16]=3)[C:10](=[O:15])[CH2:11]2)(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 234473893-(Bromomethyl)benzene-1-sulfonyl chlorideHCID 23447422HCID 23447422, compound

Product 1

HCID 23447331HCID 23447331, compound

Procedure

A solution of 4-[3-(bromomethyl)benzenesulfonyl]-1-(4-cyanobenzyl)-2-piperazinone (1.21 g) obtained from 1-(4-cyanobenzyl)-2-piperazinone hydrochloride and 3-(bromomethyl)benzenesulfonyl chloride according to a method described in Reference Example 6 and imidazole (613 mg) in DMF (20 ml) was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure, and to the residue was added ethyl acetate. The mixture was washed with sodium bicarbonate solution and saturated brine, dried (MgSO4) and concentrated, and the residue was purified with silica gel column chromatography (ethyl acetate:methanol containing 10% ammonia solution=85:15) to give pale yellow amorphous of 1-(4-cyanobenzyl)-4-[3-(1H-imidazol-1-ylmethyl)benzenesulfonyl]-2-piperazinone (734 mg).

Sources & evidence

ORD record
ord-75a2dd63de79408e85f9dcf22fd3ccc3
Source dataset
uspto-grants-2002_06
Patent number
US06403595B1

Reaction notes

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