1-Phenylpiperazine → 2-[2-(4-phenylpiperazin-1-yl)ethyl]isoindole-1,3-dione

HRID 1610034Notes

Reaction equation

HRID 1610034 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrCC[CH2:16][CH2:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28].C([O-])([O-])=O.[K+].[K+]>CCN(CC)CC.CN(C=O)C>[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:16][CH2:17][N:18]3[C:22](=[O:23])[C:21]4=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]4[C:19]3=[O:28])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 70961-PhenylpiperazineHCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimide

Product 1

HCID 85979842-[2-(4-phenylpiperazin-1-yl)ethyl]isoindole-1,3-dione

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

1-Phenylpiperazine 2 (2.21 g, 7.81 mmol) was reacted with N-(4-bromobutyl)phthalimide (1.26 g, 7.81 mmol) in the presence of K2CO3 (8.0 g) in Et3N (1.0 mL) and DMF (20 mL) to give a yellow solid 3a, 2.70 (95%) (Procedure A). 1H NMR (CDCl3) 1.55-1.82 (m, 4H, CH2CH2), 2.40-2.45 (t, J=7.5 Hz, 2H, NCH2), 2.57-2.61 (t, J=4.8 Hz, 4H, N(CH2)2), 3.17-3.20 (t, J=4.8 Hz, 4H, N(CH2)2), 3.71-3.75 (t, J=6.7 Hz, 2H, NCH2), 6.82-6.94 (3H, Ar—H), 7.23-7.28 (m, 2H, Ar—H), 7.70-7.74 (m, 2H, Ar—H), 7.83-7.86 (m, 2H, Ar—H).

Sources & evidence

ORD record
ord-050da64afb7e49159d25b42002b6bb86
Source dataset
uspto-grants-2006_01
Patent number
US06982332B2

Reaction notes

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