1-(2,4-Xylyl)piperazine → [4-(2,4-Dimethylphenyl)piperazin-1-yl][4-(1,1-dioxo-1lambda6-isothiazolidin-2-ylmethyl)phenyl]methanone

HRID 2411467Notes

Reaction equation

HRID 2411467 reaction equation
[O:1]=[S:2]1(=[O:17])[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1.[CH3:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=1[N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.O>[CH3:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=1[N:26]1[CH2:27][CH2:28][N:29]([C:12]([C:11]2[CH:10]=[CH:9][C:8]([CH2:7][N:3]3[CH2:4][CH2:5][CH2:6][S:2]3(=[O:1])=[O:17])=[CH:16][CH:15]=2)=[O:14])[CH2:30][CH2:31]1

Participants

7

Reactant 4

HCID 705441-(2,4-Xylyl)piperazineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 246888894-(1,1-Dioxo-1lambda6-isothiazolidin-2-ylmethyl)benzoic acid

Product 1

HCID 71261252[4-(2,4-Dimethylphenyl)piperazin-1-yl][4-(1,1-dioxo-1lambda6-isothiazolidin-2-ylmethyl)phenyl]methanoneYield 57.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-(1,1-Dioxo-1λ6-isothiazolidin-2-ylmethyl)benzoic acid (268 mg) described in Preparation Example 18, 1-(2,4-dimethylphenyl)piperazine (199 mg), 1-hydroxybenzotriazole 1 hydrate (142 mg) were dissolved in N,N-dimethylformamide (5 mL), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (202 mg) was added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (chloroform:methanol) to give the title compound (256 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customthe solvent was evaporated
  4. customThe obtained residue was purified by column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-2175bde86e714fd89cc46be2620520dc
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

Loading…