1,4-Butanediol → N-(1-Benzylpiperdin-4-yl)-N-isopropyl 2-(4-Hydroxybut-1-oxy)acetamide

HRID 1181519노트

반응식

HRID 1181519 반응식
[CH2:1]([OH:6])[CH2:2][CH2:3][CH2:4][OH:5].[OH-].[Na+].[CH2:9]([N:16]1[CH2:21][CH2:20][CH:19]([N:22]([CH:27]([CH3:29])[CH3:28])[C:23](=[O:26])[CH2:24]Cl)[CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)(C)(C)C>[CH2:9]([N:16]1[CH2:17][CH2:18][CH:19]([N:22]([CH:27]([CH3:29])[CH3:28])[C:23](=[O:26])[CH2:24][O:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:6])[CH2:20][CH2:21]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

참가 물질

5

반응물 3

HCID 80641,4-ButanediolHCID 14798Sodium Hydroxide2회HCID 66565165N-(1-Benzyl-piperidin-4-yl)-2-chloro-N-isopropyl-acetamide

생성물 1

HCID 67428348N-(1-Benzylpiperdin-4-yl)-N-isopropyl 2-(4-Hydroxybut-1-oxy)acetamide수율 81%

시약·촉매·용매 1

HCID 6386tert-Butanol용매2회

실험 절차

1,4-Butanediol (16 mL, 178 mmol) was refluxed with sodium hydroxide (970 mg, 24.3 mmol) in tert-butanol (8 mL) for 2 h at which time the solid sodium hydroxide had dissolved. The solution was then cooled to room temperature and a solution of N-(1-benzylpiperdin-4-yl)-N-isopropyl 2-chloroacetamide (5.0 g, 16.2 mmol) in tert-butanol (8 mL) was added dropwise. The reaction mixture was then stirred at room temperature overnight. After removal of tert-butanol under reduced pressure, the residue was dissolved in dichloromethane and this solution washed with sodium bicarbonate, water and brine. The organic layer was then dried over magnesium sulfate and concentrated. The residue was purified by flash column chromatography (dichloromethane/methanol/ammonium hydroxide: 90/9/1) to give 4.73 g of the title intermediate as a viscous oil (81% yield).

후처리

  1. dissolutionhad dissolved
  2. customAfter removal of tert-butanol under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washthis solution washed with sodium bicarbonate, water and brine
  5. dry with materialThe organic layer was then dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (dichloromethane/methanol/ammonium hydroxide: 90/9/1)

출처 및 근거

ORD 기록
ord-893795456c6748fa88917214a6d5fe7a
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07285564B2

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