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

HRID 1840602Notes

Reaction equation

HRID 1840602 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-ba86d92651f0441ca23e321ca63872e7
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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