Potassium Carbonate → N-(1-(4-formylbenzyl)piperidin-4-yl)-N-isopropylacetamide

HRID 591790ノート

反応式

HRID 591790 の反応式
BrC[CH2:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.C([O-])([O-])=O.[K+].[K+].[CH:18]([N:21]([CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)[C:22](=[O:24])[CH3:23])([CH3:20])[CH3:19]>CN(C=O)C>[CH:8]([C:7]1[CH:6]=[CH:5][C:4]([CH2:3][N:28]2[CH2:29][CH2:30][CH:25]([N:21]([CH:18]([CH3:20])[CH3:19])[C:22](=[O:24])[CH3:23])[CH2:26][CH2:27]2)=[CH:11][CH:10]=1)=[O:9]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 110851354-(2-Bromoethyl)benzaldehydeHCID 23369939N-isopropyl-N-(piperidin-4-yl)acetamide

生成物 1

HCID 86662036N-(1-(4-formylbenzyl)piperidin-4-yl)-N-isopropylacetamide収率 61%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 4-(bromoethyl)benzaldehyde (0.840 g, 4.2 mmol) and K2CO3 (1.75 g, 12.6 mmol) in DMF (15 mL) was added N-isopropyl-N-(piperidin-4-yl)acetamide (0.92 g, 4.2 mmol) and the reaction was stirred at room temperature 5 hours, then concentrated in vacuo. The resulting mixture was diluted with H2O and extracted with EtOAc. The organics were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 1% to 10% MeOH/CH2Cl2, afforded N-(1-(4-formylbenzyl)piperidin-4-yl)-N-isopropylacetamide (0.770 g, 61%).

後処理

  1. concentrationconcentrated in vacuo
  2. additionThe resulting mixture was diluted with H2O
  3. extractionextracted with EtOAc
  4. washThe organics were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica gel
  9. washeluting with 1% to 10% MeOH/CH2Cl2

出典と根拠

ORDレコード
ord-510d241cc99b49c193ede95e9eabbcd2
出典データセット
uspto-grants-2016_01
特許番号
US09238640B2

反応ノート

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