Water → 1-(2-propenyl)-4-(N-2-propylcarbamoyl)-2-piperazinone

HRID 1162809ノート

反応式

HRID 1162809 の反応式
Cl.[CH2:2]([N:5]1[CH2:10][CH2:9][NH:8][CH2:7][C:6]1=[O:11])[CH:3]=[CH2:4].C(N(C(C)C)CC)(C)C.[CH3:21][CH:22]([N:24]=[C:25]=[O:26])[CH3:23].O>ClCCl>[CH2:2]([N:5]1[CH2:10][CH2:9][N:8]([C:25](=[O:26])[NH:24][CH:22]([CH3:23])[CH3:21])[CH2:7][C:6]1=[O:11])[CH:3]=[CH2:4]

参加物

6

反応物 4

HCID 962WaterHCID 61277Isopropyl isocyanateHCID 81531DiisopropylethylamineHCID 684328741-(Prop-2-en-1-yl)piperazin-2-one hydrochloride

生成物 1

HCID 684331521-(2-propenyl)-4-(N-2-propylcarbamoyl)-2-piperazinone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 1-(2-propenyl)-2-piperazinone hydrochloride (7.9 g, 44 mmol) and diisopropylethylamine (8 mL, 46 mmol) in dichloromethane (100 mL) was added 2-propylisocyanate (5.6 g, 66 mmol). The mixture was stirred at ambient temperature for 18 h. Water (75 mL) was added, and the organic layer was collected, dried (MgSO4), filtered. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography using a gradient elution of 2%, 3%, 4% MeOH in CH2Cl2. Product-containing fractions were combined and concentrated in vacuo to yield 1-(2-propenyl)-4-(N-2-propylcarbamoyl)-2-piperazinone as a solid. HPLC RT=2.17 min (Mehtos A); ES MS (M+H)=226; 1H NMR (400 MHz, CDCl3) δ 5.75 (ddt, 1H), 5.2 (overlapping doublets, 2H), 4.32 (b rd, 1H), 4.04 (d, J=6 Hz, 2H), 3.97 (s, 2H), 3.67 (t, J=7 Hz, 2H), 3.33 (t, J=7 hz, 2H), 1.16 (d, J=7 Hz, 6H).

後処理

  1. customthe organic layer was collected
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by silica gel column chromatography
  6. washa gradient elution of 2%, 3%, 4% MeOH in CH2Cl2
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6cf01c19b9664c7993a6dc78b5c9cd09
出典データセット
uspto-grants-2010_10
特許番号
US07820680B2

反応ノート

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