Formaldehyde → 1-(2-diethylaminomethyl-5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)-6-phenylhexan-1-one

HRID 611172

반응식

HRID 611172 반응식
[O:1]1[C:5]2[CH2:6][N:7]([C:10](=[O:22])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:8][CH2:9][C:4]=2[CH:3]=[CH:2]1.[CH2:23]([NH:25][CH2:26][CH3:27])[CH3:24].[CH2:28]=O>C(O)(=O)C>[CH2:23]([N:25]([CH2:28][C:2]1[O:1][C:5]2[CH2:6][N:7]([C:10](=[O:22])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:8][CH2:9][C:4]=2[CH:3]=1)[CH2:26][CH3:27])[CH3:24]

참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 8021DiethylamineHCID 196001451-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)-6-phenylhexan-1-one

생성물 1

HCID 196001221-(2-diethylaminomethyl-5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)-6-phenylhexan-1-one

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
100 °C

실험 절차

To a solution of 0.322 g (1.083 mmol) of 1-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)-6-phenylhexan-1-one in 20 ml of acetic acid, 0.13 g (1.3 mmol) of diethylamine and 0.11 g (1.3 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 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. distillationAfter the solvent was distilled off under reduced pressure
  2. extractionextracted with dichloromethane 3 times
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. 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-14f5b9ca8a61463a959f249b7019aef9
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998433

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