Dimethylamine → N,N-Dimethyl-(5-[4-(4-methoxybenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[3,2-c]pyridin-2-ylmethyl]amine

HRID 611262노트

반응식

HRID 611262 반응식
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([C:7]([C:9]2[CH:25]=[CH:24][C:12]([C:13]([N:15]3[CH2:20][CH2:19][C:18]4[O:21][CH:22]=[CH:23][C:17]=4[CH2:16]3)=[O:14])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.[CH3:28][NH:29][CH3:30].[CH2:31]=O>C(O)(=O)C>[CH3:28][N:29]([CH2:31][C:22]1[O:21][C:18]2[CH2:19][CH2:20][N:15]([C:13](=[O:14])[C:12]3[CH:24]=[CH:25][C:9]([C:7](=[O:8])[C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:27][CH:26]=4)=[CH:10][CH:11]=3)[CH2:16][C:17]=2[CH:23]=1)[CH3:30]

참가 물질

5

반응물 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 196002365-[4-(4-Methoxybenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[3,2-c]pyridine

생성물 1

HCID 19600124N,N-Dimethyl-(5-[4-(4-methoxybenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[3,2-c]pyridin-2-ylmethyl]amine

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
100 °C

실험 절차

To a solution of 0.350 g (0.968 mmol) of 5-[4-(4-methoxybenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[3,2-c]pyridine in 10 ml of acetic acid, 0.131 ml (1.45 mmol) of 50% aqueous dimethylamine and 0.118 ml (1.45 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 90 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with 5% aqueous sodium hydrogen carbonate 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 (chloroform/methanol=50/1 to 25/1). This was washed with diethyl ether 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 (chloroform/methanol=50/1 to 25/1)
  7. washThis was washed with diethyl ether

출처 및 근거

ORD 기록
ord-5e3d11b9c27149d7b5855765c307da43
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998433

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