Triethylamine → 2-(4-Methylpiperazin-1-yl)-ethyl 4-(2-methylphenyl)piperazine-1-carboxylate

HRID 417971

반응식

HRID 417971 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(CC)CC.Cl.Cl.[CH3:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1>CN(C=O)C>[NH3:5].[CH3:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[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

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 919641-(o-Tolyl)piperazine dihydrochlorideHCID 574450072-(4-Methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate2회

생성물 2

HCID 222AmmoniaHCID 426356252-(4-Methylpiperazin-1-yl)-ethyl 4-(2-methylphenyl)piperazine-1-carboxylate수율 63.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2-(4-Methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate (Intermediate 4; 866 mg, 2.8 mmol) was dissolved in DMF (20 mL). NEt3 (1.5 mL, 10.8 mmol) and 4-(2-methyl-phenyl)piperazine dihydrochloride (704 mg, 2.8 mmol) were added and the reaction mixture was stirred at room temperature for 24 hours, and the reaction mixture was then concentrated in vacuo. The resulting residue was dissolved in EtOAc (50 mL) and washed with 1 M aq Na2CO3 solution (5×50 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by normal phase column chromatography (eluting with DCM, followed by a 200:8:1 mixture of DCM:EtOH:NH3) to give 2-(4-methylpiperazin-1-yl)-ethyl 4-(2-methylphenyl)piperazine-1-carboxylate (308 mg, 32%) as a yellow oil.

후처리

  1. concentrationthe reaction mixture was then concentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in EtOAc (50 mL)
  3. washwashed with 1 M aq Na2CO3 solution (5×50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by normal phase column chromatography (
  7. washeluting with DCM
  8. additionfollowed by a 200:8:1 mixture of DCM

출처 및 근거

ORD 기록
ord-c0c8dd23ff8445d6b7dbdd024fa46b42
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093248B2

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