Water → HCID 21830850、化合物

HRID 2393430ノート

反応式

HRID 2393430 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH2:19][CH3:20])CC)C.C([CH:23]([C:27](Cl)=[O:28])[C:24](Cl)=[O:25])C.[OH2:30]>ClCCl.C(OCC)C>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:27](=[O:28])[CH2:23][C:24]([O:25][CH2:19][CH3:20])=[O:30])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 759941-BenzylpiperazineHCID 109209242-Ethylpropanedioyl dichloride

生成物 1

HCID 21830850HCID 21830850、化合物収率 58%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
-20 °C

実験手順

To a cooled (-20° C.) and stirred solution of N-benzylpiperazine (10 g, 56.7 mmol) and triethylamine (8.7 ml, 62.4 mmol) in dichloromethane (200 ml) was added ethyl malonyl chloride (8.5 ml, 66.4 mmol) over 10 minutes, under nitrogen. The mixture was allowed to warm to room temperature and it was stirred for 1 hour before water (100 ml) and diethyl ether (500 ml) were added. The organic phase was decanted off, washed with water (1×70 ml), 10% aqueous sodium bicarbonate (1×75 ml), brine (1×75 ml), then dried (MgSO4) and concentrated. Flash chromatography of the residue (silica gel, ethyl acetate--ethanol, 95:5) afforded 9.53 g, (58%) of the title compound as a colourless oil. δ (360 MHz, CDCl3), 1.28 (3H, t, J=7.2Hz), 2.48 (4H, br s), 3.45 (2H, s) 3.47 (2H, br s), 3.56 (2H, br s), 3.68 (2H, br s), 4.19 (2H, q, J=7.2Hz), 7.24-7.36 (5H, m); m/e (ES) 291 (M+1)+.

後処理

  1. temperatureto warm to room temperature
  2. additionwere added
  3. customThe organic phase was decanted off
  4. washwashed with water (1×70 ml), 10% aqueous sodium bicarbonate (1×75 ml), brine (1×75 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-9f525cdd5bac4aeeb95c023eb26063bc
出典データセット
uspto-grants-1998_09
特許番号
US05807857

反応ノート

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