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

HRID 417968

反応式

HRID 417968 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-e3baaee6b1f2426fad3952ca369662ae
出典データセット
uspto-grants-2012_01
特許番号
US08093248B2

関連ノート

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