Dimethylamine → 1-(2-dimethylaminomethyl-5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)decan-1-one

HRID 611085ノート

反応式

HRID 611085 の反応式
[O:1]1[C:5]2[CH2:6][N:7]([C:10](=[O:20])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:8][CH2:9][C:4]=2[CH:3]=[CH:2]1.[CH3:21][NH:22][CH3:23].[CH2:24]=O>C(O)(=O)C>[CH3:21][N:22]([CH2:24][C:2]1[O:1][C:5]2[CH2:6][N:7]([C:10](=[O:20])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:8][CH2:9][C:4]=2[CH:3]=1)[CH3:23]

参加物

5

反応物 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 196000951-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)decan-1-one

生成物 1

HCID 196000581-(2-dimethylaminomethyl-5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)decan-1-one

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

To a solution of 0.230 g (0.829 mmol) of 1-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)decan-1-one in 20 ml of acetic acid, 0.090 ml (1.0 mmol) of 50% aqueous dimethylamine and 0.080 ml (1.0 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 1.5 hours. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with aqueous sodium hydroxide and extracted with dichloromethane 2 times. The combined organic layer was washed with water and dried over anhydrous sodium 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=9/1) to yield the desired product.

後処理

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. extractionextracted with dichloromethane 2 times
  3. washThe combined organic layer was washed with water
  4. dry with materialdried over anhydrous sodium 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=9/1)

出典と根拠

ORDレコード
ord-b80f8df76bc24eec947d5671771f0015
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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