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

HRID 611430노트

반응식

HRID 611430 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ee78eaa981214c4ba4ca988292073ab4
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998433

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