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

HRID 1162809노트

반응식

HRID 1162809 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6cf01c19b9664c7993a6dc78b5c9cd09
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820680B2

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