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 5571Notes

Reaction equation

HRID 5571 reaction equation
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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bba1b398f5164b93b56a82edcd1f84ce
Source dataset
uspto-grants-1993_09
Patent number
US05245051

Reaction notes

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