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

HRID 417968

반응식

HRID 417968 반응식
[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

참가 물질

5

반응물 3

HCID 70961-PhenylpiperazineHCID 81531DiisopropylethylamineHCID 574450072-(4-Methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate2회

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-e3baaee6b1f2426fad3952ca369662ae
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093248B2

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