Dimethylamine → 2-dimethylaminomethyl-5-(6-phenylhexyl)-6,7-dihydro-5H-furo[3,2-c]pyridin-4-one

HRID 611430ノート

反応式

HRID 611430 の反応式
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][C:16]3[O:19][CH:20]=[CH:21][C:15]=3[C:14]2=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:23][NH:24][CH3:25].[CH2:26]=O>C(O)(=O)C>[CH3:23][N:24]([CH2:26][C:20]1[O:19][C:16]2[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:14](=[O:22])[C:15]=2[CH:21]=1)[CH3:25]

参加物

5

反応物 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 196001085-(6-phenylhexyl)-6,7-dihydro-5H-furo[3,2-c]pyridin-4-one

生成物 1

HCID 195999812-dimethylaminomethyl-5-(6-phenylhexyl)-6,7-dihydro-5H-furo[3,2-c]pyridin-4-one

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a solution of 0.242 g (0.814 mmol) of 5-(6-phenylhexyl)-6,7-dihydro-5H-furo[3,2-c]pyridin-4-one in 10 ml of acetic acid, 0.37 g (4.1 mmol) of 50% aqueous dimethylamine and 0.33 g (4.1 mmol) of 37% aqueous formaldehyde were added, followed by overnight refluxing. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide and extracted with ethyl acetate 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=4/1) to yield the desired product.

後処理

  1. temperaturerefluxing
  2. distillationAfter the solvent was distilled off under reduced pressure
  3. extractionextracted with ethyl acetate 3 times
  4. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=4/1)

出典と根拠

ORDレコード
ord-ee78eaa981214c4ba4ca988292073ab4
出典データセット
uspto-grants-1999_12
特許番号
US05998433

反応ノート

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