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

HRID 611085노트

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HRID 611085 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b80f8df76bc24eec947d5671771f0015
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998433

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