Potassium Carbonate → Ethyl 3-[4-(3,3-diphenyl-1-propyl)piperazin-1-yl]benzoate

HRID 1836806Notes

Reaction equation

[N:1]1([C:7]2[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[C:24]1([CH:30]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:31][CH2:32]Br)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C=O>[C:24]1([CH:30]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:31][CH2:32][N:4]2[CH2:3][CH2:2][N:1]([C:7]3[CH:8]=[C:9]([CH:15]=[CH:16][CH:17]=3)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH2:5]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 70 °C

Procedure

The compound (1.60 g) prepared in step (a) was dissolved in N,N-dimethylformamide (20 ml). Potassium carbonate (2.79 g) and 3,3-diphenylpropyl bromide (2.82 g) were added to the solution. The mixture was stirred at 70° C. for 8 hr. The reaction solution was extracted with ethyl acetate, followed by washing with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:ethyl acetate=5:1) to give 2.00 g (71.3%) of ethyl 3-[4-(3,3-diphenyl-1-propyl)piperazin-1-yl]benzoate.

Workup

extractionThe reaction solution was extracted with ethyl acetate
washby washing with water and saturated brine
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
customthe solvent was then removed by distillation under the reduced pressure
customThe residue was purified by column chromatography on silica gel (chloroform:ethyl acetate=5:1)

Sources & evidence

ORD record: ord-17b2f3d9640a463ea904568f0a841032
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777414B1

Reaction notes

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