1-Benzylpiperazine → 2-(4-Methylpiperazin-1-yl)ethyl 4-benzylpiperazine-1-carboxylate

HRID 417977

반응식

HRID 417977 반응식
[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]=1

참가 물질

5

반응물 3

HCID 759941-BenzylpiperazineHCID 81531DiisopropylethylamineHCID 574450072-(4-Methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate2회

생성물 1

HCID 426357982-(4-Methylpiperazin-1-yl)ethyl 4-benzylpiperazine-1-carboxylate수율 60%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc (40 mL)
  3. washwashed with 1 M aq Na2CO3 solution (6×50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by reverse phase chromatography (gradient eluting with MeOH in water, 0-100%)

출처 및 근거

ORD 기록
ord-8af6a36b2aa94be18cd36b677ac064e1
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093248B2

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