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

HRID 611132
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HRID 611132 반응식
[CH2:1]([C:8]1[CH:24]=[CH:23][C:11]([C:12]([N:14]2[CH2:19][CH2:18][C:17]3[CH:20]=[CH:21][O:22][C:16]=3[CH2:15]2)=[O:13])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:25][NH:26][CH3:27].[CH2:28]=O>C(O)(=O)C>[CH3:25][N:26]([CH2:28][C:21]1[O:22][C:16]2[CH2:15][N:14]([C:12](=[O:13])[C:11]3[CH:23]=[CH:24][C:8]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:9][CH:10]=3)[CH2:19][CH2:18][C:17]=2[CH:20]=1)[CH3:27]
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참가 물질

5

반응물 3

HCID 674Dimethylamine2회HCID 712Formaldehyde2회HCID 195999886-(4-Heptylbenzoyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

생성물 1

HCID 19600030N,N-dimethyl-[6-(4-heptylbenzoyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-2-ylmethyl]amine

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
100 °C

실험 절차

To a solution of 0.260 g (0.799 mmol) of 6-(4-heptylbenzoyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine in 20 ml of acetic acid, 0.108 ml (1.20 mmol) of 50% aqueous dimethylamine and 0.097 ml (1.20 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 60 minutes. Additionally, 0.072 ml (0.799 mmol) of 50% aqueous dimethylamine and 0.064 ml (0.799 mmol) of 37% aqueous formaldehyde were added, followed by stirring for 30 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with 5% aqueous solution of 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 to chloroform/methanol=50/1 to 25/1) to yield the desired product.

후처리

  1. stirringby stirring for 30 minutes
  2. distillationAfter the solvent was distilled off under reduced pressure
  3. extractionextracted with dichloromethane 2 times
  4. washThe combined organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting crude product was purified by silica gel column chromatography (chloroform to chloroform/methanol=50/1 to 25/1)

출처 및 근거

ORD 기록
ord-64fcc190066646e3982273be758a6a8e
출처 데이터셋
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05998433

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