Piperidine → 3-Piperidin-1-yl-N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-propionamide

HRID 643265ノート

反応式

HRID 643265 の反応式
[CH3:1][C:2]12[CH2:22][CH:6]([N:7]([C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:21])[CH:19]=[CH2:20])=[CH:13][CH:12]=3)=[O:10])[CH2:8]1)[CH2:5][C:4]([CH3:24])([CH3:23])[CH2:3]2.[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>CCO>[N:25]1([CH2:20][CH2:19][C:18]([NH:17][C:14]2[CH:13]=[CH:12][C:11]([C:9]([N:7]3[CH2:8][C:2]4([CH3:1])[CH2:22][CH:6]3[CH2:5][C:4]([CH3:24])([CH3:23])[CH2:3]4)=[O:10])=[CH:16][CH:15]=2)=[O:21])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

参加物

4

反応物 2

HCID 8082PiperidineHCID 68429631N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-acrylamide

生成物 1

HCID 112236473-Piperidin-1-yl-N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-propionamide収率 22%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
100 °C

実験手順

To a mixture of N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-acrylamide (0.2 g, 0.613 mmol) and piperidine (120 μl, 1.23 mmol) in EtOH (10 ml) was added two drops of TEA. The resulting mixture was heated in a microwave oven at 100° C. for 25 min. The volatiles were evaporated in vacuo and the residue purified on column chromatography (silicagel) using first EtOAc followed by 4% TEA in EtOAc-EtOH 9:1 as eluents. Semi pure fractions were collected, the solvent evaporated in vacuo and the residue dissolved in 1 N HCl (2.5 ml). Water (5 ml) was added followed by diethyl ether (10 ml) and the mixture was stirred for 30 min. The organic phase was discarded and the pH of the aqueous phase adjusted to 10 with 1 N NaOH followed by extraction with diethyl ether (2×10 ml). The combined organic phases were dried (Na2SO4), filtered and evaporated in vacuo affording 55 mg (22%) of the title compound as an oil.

後処理

  1. customThe volatiles were evaporated in vacuo
  2. customthe residue purified on column chromatography (silicagel)
  3. customSemi pure fractions were collected
  4. customthe solvent evaporated in vacuo
  5. dissolutionthe residue dissolved in 1 N HCl (2.5 ml)
  6. additionWater (5 ml) was added
  7. extractionfollowed by extraction with diethyl ether (2×10 ml)
  8. dry with materialThe combined organic phases were dried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated in vacuo

出典と根拠

ORDレコード
ord-29cffb24defb4b92a22594edbba502e2
出典データセット
uspto-grants-2010_04
特許番号
US07700583B2

反応ノート

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