1-Phenylpiperazine → 2-(4-Methyl-piperazin-1-yl)ethyl 4-phenylpiperazine-1-carboxylate formate

HRID 417968

Reaction equation

HRID 417968 reaction equation
[C:1](=[O:22])([O:12]C1C=CC([N+]([O-])=O)=CC=1)[O:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH3:11])[CH2:7][CH2:6]1.CCN(C(C)C)C(C)C.[C:32]1([N:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C=O)C>[CH:1]([OH:12])=[O:2].[C:32]1([N:38]2[CH2:43][CH2:42][N:41]([C:1]([O:2][CH2:3][CH2:4][N:5]3[CH2:6][CH2:7][N:8]([CH3:11])[CH2:9][CH2:10]3)=[O:22])[CH2:40][CH2:39]2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 70961-PhenylpiperazineHCID 81531DiisopropylethylamineHCID 574450072-(4-Methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate2×

Product 1

HCID 666509882-(4-Methyl-piperazin-1-yl)ethyl 4-phenylpiperazine-1-carboxylate formateYield 11.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-Methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate (Intermediate 4; 1.58 g, 5.1 mmol) was dissolved in DMF (25 mL). DIPEA (0.87 mL, 5.0 mmol) and 4-phenyl-piperazine (807 mg, 0.76 mL, 5.0 mmol) were added and the reaction mixture was stirred at room temperature for 14 hours. The reaction mixture was then concentrated in vacuo. The residue was purified by reverse phase column chromatography (gradient eluting with MeOH in water, with 1% formic acid in each solvent, 0-100%) to give 2-(4-methyl-piperazin-1-yl)ethyl 4-phenylpiperazine-1-carboxylate formate (113 mg, 6.7%) as a yellow oil.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customThe residue was purified by reverse phase column chromatography (gradient
  3. washeluting with MeOH in water, with 1% formic acid in each solvent, 0-100%)

Sources & evidence

ORD record
ord-e3baaee6b1f2426fad3952ca369662ae
Source dataset
uspto-grants-2012_01
Patent number
US08093248B2

Linked notes

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