6-[3-[[(6,7-Dihydro-1,3-dioxolo[4,5-g][1,4]benzodioxin-6-yl)methyl]amino]propoxy]chromen-4-one hydrochloride → N-[3-(Chroman-6-yloxy)-propyl]-6,7-dihydro-1,3-dioxolo[4,5-g][1,4]benzodioxin-6-methanamine

HRID 5571노트

반응식

HRID 5571 반응식
Cl.[O:2]1[C:31]2[C:5](=[CH:6][C:7]3[O:12][CH:11]([CH2:13][NH:14][CH2:15][CH2:16][CH2:17][O:18][C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[O:25][CH:24]=[CH:23][C:22]5=O)[CH2:10][O:9][C:8]=3[CH:30]=2)[O:4][CH2:3]1.Cl.CC(O)C>CO.[Pd]>[O:25]1[C:26]2[C:21](=[CH:20][C:19]([O:18][CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH:11]3[CH2:10][O:9][C:8]4[CH:30]=[C:31]5[O:2][CH2:3][O:4][C:5]5=[CH:6][C:7]=4[O:12]3)=[CH:28][CH:27]=2)[CH2:22][CH2:23][CH2:24]1

참가 물질

5

반응물 2

HCID 197967656-[3-[[(6,7-Dihydro-1,3-dioxolo[4,5-g][1,4]benzodioxin-6-yl)methyl]amino]propoxy]chromen-4-one hydrochlorideHCID 21912024Isopropanol hydrochloride

생성물 1

HCID 19796755N-[3-(Chroman-6-yloxy)-propyl]-6,7-dihydro-1,3-dioxolo[4,5-g][1,4]benzodioxin-6-methanamine수율 56.3%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

6-[3-[[(6,7-Dihydro-1,3-dioxolo[4,5-g][1,4]benzodioxin-6-yl)methyl]amino]propoxy]chromen-4-one hydrochloride (0.9 g, 2.0 mmole), prepared in Example 5 above, was dissolved in 50 ml of methanol and 4N HCl/IPA (12.5 ml, 50 mmole) and 10% Palladium on Carbon (0.2 g) were added. The mixture was hydrogenated on a Parr apparatus for 24 hours and 4 psi of hydrogen was absorbed. Water (10 ml) was added to dissolved the resulting mixture and the catalyst was removed by filteration. The filtrate was concentrated, and the residue was treated with saturated aqueous sodium bicarbonate and extracted with dichloromethane. The extract was washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude product was chromatographed on a silica gel column using 5% methanol in dichloromethane as an eluent. The product-containing fractions (Rf=0.47 on silica gel with 5% chloroform/methanol) were combined, concentrated, dissolved in methanol and acidified with 4N HCl/IPA until the solution was 3 in pH. The resulting precipitate was collected on a Buchner funnel and recrystallized from methanol to give 0.45 g of title compound as a white solid hydrochloride, m.p. 217°-218° C.

후처리

  1. custom4 psi of hydrogen was absorbed
  2. additionWater (10 ml) was added
  3. dissolutionto dissolved the resulting mixture
  4. customthe catalyst was removed by filteration
  5. concentrationThe filtrate was concentrated
  6. additionthe residue was treated with saturated aqueous sodium bicarbonate
  7. extractionextracted with dichloromethane
  8. washThe extract was washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe crude product was chromatographed on a silica gel column
  13. concentrationconcentrated
  14. dissolutiondissolved in methanol
  15. customThe resulting precipitate was collected on a Buchner funnel
  16. customrecrystallized from methanol

출처 및 근거

ORD 기록
ord-bba1b398f5164b93b56a82edcd1f84ce
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05245051

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