Reaction equation
[C:1](=[O:22])(OC1C=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.[CH2:32]([N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C=O)C>[CH2:32]([N:39]1[CH2:44][CH2:43][N:42]([C:1]([O:2][CH2:3][CH2:4][N:5]2[CH2:6][CH2:7][N:8]([CH3:11])[CH2:9][CH2:10]2)=[O:22])[CH2:41][CH2:40]1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1Participants
5
Procedure
2-(4-Methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate (Intermediate 4; 567 mg, 1.8 mmol) was dissolved in DMF (15 mL). DIPEA (0.52 mL, 3.0 mmol) and 4-benzyl-piperazine (0.296 mL, 1.7 mmol) were added. The reaction mixture was stirred at room temperature for 24 hours and then concentrated in vacuo. The residue was dissolved in EtOAc (40 mL) and washed with 1 M aq Na2CO3 solution (6×50 mL), dried (MgSO4) and concentrated in vacuo. The crude product was purified by reverse phase chromatography (gradient eluting with MeOH in water, 0-100%) to give 2-(4-methylpiperazin-1-yl)ethyl 4-benzylpiperazine-1-carboxylate (352 mg, 60% yield) as a colourless oil.
Workup
- concentrationconcentrated in vacuo
- dissolutionThe residue was dissolved in EtOAc (40 mL)
- washwashed with 1 M aq Na2CO3 solution (6×50 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customThe crude product was purified by reverse phase chromatography (gradient eluting with MeOH in water, 0-100%)
Sources & evidence
- ORD record
- ord-8af6a36b2aa94be18cd36b677ac064e1
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093248B2
Linked notes
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