4-Methylmorpholine → 2-(4-Methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate

HRID 417949

反応式

HRID 417949 の反応式
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[CH3:14][N:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][OH:23])[CH2:17][CH2:16]1.CN1CCOCC1>C(Cl)Cl>[C:2](=[O:3])([O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1)[O:23][CH2:22][CH2:21][N:18]1[CH2:19][CH2:20][N:15]([CH3:14])[CH2:16][CH2:17]1

参加物

5

反応物 3

HCID 79724-MethylmorpholineHCID 821294-Nitrophenyl chloroformateHCID 2311841-(2-Hydroxyethyl)-4-methylpiperazine

生成物 1

HCID 574450072-(4-Methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate収率 71%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

4-Nitrophenyl chloroformate (9.85 g, 49 mmol) was dissolved in DCM (200 mL), and cooled to 0° C. 2-(4-methylpiperazin-1-yl)ethanol (7.2 g, 50 mmol) and NMM (6 mL) were added, and the reaction mixture was allowed to warm gradually to room temperature over 16 hours. The reaction mixture was washed with 1M aq Na2CO3 solution until the yellow colour extracted into the aqueous layer had disappeared. The organic phase was dried (MgSO4), filtered and concentrated in vacuo to give 2-(4-methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate (10.7 g, 71%) as a yellow oil which solidified on standing.

後処理

  1. temperatureto warm gradually to room temperature over 16 hours
  2. washThe reaction mixture was washed with 1M aq Na2CO3 solution until the yellow colour
  3. extractionextracted into the aqueous layer
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8ad9bf268d63479fb27969f8cffcb832
出典データセット
uspto-grants-2012_01
特許番号
US08093248B2

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