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 5571ノート

反応式

HRID 5571 の反応式
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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bba1b398f5164b93b56a82edcd1f84ce
出典データセット
uspto-grants-1993_09
特許番号
US05245051

反応ノート

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