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

HRID 659080ノート

反応式

HRID 659080 の反応式
[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

参加物

5

反応物 3

HCID 80641,4-ButanediolHCID 14798Sodium Hydroxide2 回HCID 66565165N-(1-Benzyl-piperidin-4-yl)-2-chloro-N-isopropyl-acetamide

生成物 1

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

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒2 回

実験手順

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-benzylpiperidin-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).

後処理

  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)

出典と根拠

ORDレコード
ord-a660384875574e559e76418d489a43e5
出典データセット
uspto-grants-2011_12
特許番号
US08080565B2

反応ノート

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