Ethyl Acetate → HCID 15143638, compound

HRID 1086241Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:26]=[CH:25][C:11]([CH:12]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][CH:9]=1.[CH3:27][C:28]1[CH:33]=[C:32]([CH3:34])[CH:31]=[C:30]([CH3:35])[C:29]=1[NH:36][C:37](=[O:40])[CH2:38]Cl.C(OCC)(=O)C>CN(C)C=O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH:12]([N:19]2[CH2:20][CH2:21][N:22]([CH2:38][C:37](=[O:40])[NH:36][C:29]3[C:28]([CH3:27])=[CH:33][C:32]([CH3:34])=[CH:31][C:30]=3[CH3:35])[CH2:23][CH2:24]2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2 g of anhydrous potassium carbonate were added to a mixture of 192.6 mg of 1-(4-chlorobenzhydryl)piperazine and 142.7 mg of N-(2,4,6-trimethylphenyl)chloroacetamide dissolved in 20 ml of N,N-dimethylformamide, and the reaction mixture was stirred at 80° C. for 7.5 hours. At the end of this time, ethyl acetate was added to the mixture, and the organic layer was separated. The organic layer was washed three times with water, and then the solvent was evaporated off under reduced pressure. The residue was subjected to silica gel thin layer chromatography using a 1:1 by volume mixture of cyclohexane and ethyl acetate as the developing solvent, to afford a purified 1-(4-chlorobenzhydryl)-4-(2,4,6-trimethylphenylcarbamoylmethyl)piperazine.

Workup

customthe organic layer was separated
washThe organic layer was washed three times with water
customthe solvent was evaporated off under reduced pressure
additionby volume mixture of cyclohexane and ethyl acetate as the developing solvent

Sources & evidence

ORD record: ord-0ef1a17fcecb49cbbd03f5d133892f97
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05028610

Reaction notes

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