Dimethylamine → 1-(2-Dimethylaminomethyl-4,5,7,8-tetrahydrofuro[2,3-d]azepin-6-yl)-6-phenylhexan-1-one

HRID 611226노트

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HRID 611226 반응식
[O:1]1[C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:9][CH2:10][C:4]=2[CH:3]=[CH:2]1.[CH3:24][NH:25][CH3:26].[CH2:27]=O>C(O)(=O)C>[CH3:24][N:25]([CH2:27][C:2]1[O:1][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:9][CH2:10][C:4]=2[CH:3]=1)[CH3:26]

참가 물질

5

반응물 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 196000531-(4,5,7,8-Tetrahydrofuro[2,3-d]azepin-6-yl)-6-phenylhexan-1-one

생성물 1

HCID 195999231-(2-Dimethylaminomethyl-4,5,7,8-tetrahydrofuro[2,3-d]azepin-6-yl)-6-phenylhexan-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 (0.739 mmol) of 1-(4,5,7,8-tetrahydrofuro[2,3-d]azepin-6-yl)-6-phenylhexan-1-one in 20 ml of acetic acid, 80 mg (0.89 mmol) of 50% aqueous dimethylamine and 72 mg (0.89 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 30 minutes. 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-805b10d917324d4ea8b8c4dc7b2816a6
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998433

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