1-(2,4-Xylyl)piperazine → 1-(2,4-Dimethylphenyl)-4-[4-(1,1-dioxidoisothiazolidin-2-yl)benzoyl]piperazine

HRID 2411504Notes

Reaction equation

HRID 2411504 reaction equation
[O:1]=[S:2]1(=[O:16])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1.[CH3:17][C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=1[N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>>[CH3:17][C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:19]=1[N:25]1[CH2:26][CH2:27][N:28]([C:11]([C:10]2[CH:9]=[CH:8][C:7]([N:3]3[CH2:4][CH2:5][CH2:6][S:2]3(=[O:1])=[O:16])=[CH:15][CH:14]=2)=[O:13])[CH2:29][CH2:30]1

Participants

3

Reactant 2

HCID 705441-(2,4-Xylyl)piperazineHCID 66250114-(1,1-Dioxo-1,2-thiazolidin-2-yl)benzoic acid

Product 1

HCID 185915601-(2,4-Dimethylphenyl)-4-[4-(1,1-dioxidoisothiazolidin-2-yl)benzoyl]piperazineYield 88.8%

Procedure

Using 4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)benzoic acid (253 mg) described in Preparation Example 16 and 1-(2,4-dimethylphenyl)piperazine (199 mg) and by the reaction and treatment in the same manner as in Example 87, [4-(2,4-dimethylphenyl)piperazin-1-yl][4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)phenyl]methanone (384 mg) was obtained. Using the obtained [4-(2,4-dimethylphenyl)piperazin-1-yl][4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)phenyl]methanone (303 mg) and by the reaction and treatment in the same manner as in Example 123, the title compound (264 mg) was obtained.

Sources & evidence

ORD record
ord-21cfdbc1f6f44e698b4050048d4380df
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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