1-Phenylpiperazine → 1-Piperazinepropanamide, N-1,3-benzodioxol-5-yl-4-phenyl-

HRID 1788673Notes

Reaction equation

Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]2[O:13][CH2:14][O:15][C:9]=2[CH:8]=1)=[O:5].[C:16]1([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>CN(C)C=O>[C:16]1([N:22]2[CH2:27][CH2:26][N:25]([CH2:2][CH2:3][C:4]([NH:6][C:7]3[CH:12]=[CH:11][C:10]4[O:13][CH2:14][O:15][C:9]=4[CH:8]=3)=[O:5])[CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To N-(3-chloropropionyl)-3,4-methylenedioxyaniline (2.0 g) dissolved in N,N-dimethylformamide (20 ml) were added N-phenylpiperazine (1.6 g) and triethylamine (3 ml) and the mixture was stirred at 80° C. for 20 hours in a nitrogen atmosphere. The reaction mixture was evaporated in vacuo and to the residue were added ethyl acetate and 2N sodium hydroxide solution. After the aqueous layer was removed, the ethyl acetate layer was washed twice with water and dried over anhydrous sodium sulfate. The ethyl acetate was then distilled off and the residual solid was recrystallized from ethanol to give N-[3-(4-phenyl-1-piperazinyl)propionyl]-3,4-methylenedioxyaniline (3.4 g, 90% yield).

Workup

customThe reaction mixture was evaporated in vacuo and to the residue
additionwere added ethyl acetate and 2N sodium hydroxide solution
customAfter the aqueous layer was removed
washthe ethyl acetate layer was washed twice with water
dry with materialdried over anhydrous sodium sulfate
distillationThe ethyl acetate was then distilled off
customthe residual solid was recrystallized from ethanol

Sources & evidence

ORD record: ord-75fa5284301e4ade82a6428f4e925b67
Source dataset: uspto-grants-1987_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04684651

Reaction notes

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