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

HRID 417971

反応式

HRID 417971 の反応式
[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

参加物

6

反応物 3

HCID 8471TriethylamineHCID 919641-(o-Tolyl)piperazine dihydrochlorideHCID 574450072-(4-Methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate2 回

生成物 2

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

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; 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.

後処理

  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

出典と根拠

ORDレコード
ord-c0c8dd23ff8445d6b7dbdd024fa46b42
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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