7-[3-[[(2,3-Dihydro-6-phenylmethoxy-1,4-benzodioxin-2-yl)methyl]amino]propoxy]-2H-1-benzopyran-2-one hydrochloride → HCID 19778671, compound

HRID 374211Notes

Reaction equation

HRID 374211 reaction equation
Cl.C1(C[O:9][C:10]2[CH:36]=[CH:35][C:13]3[O:14][CH:15]([CH2:18][NH:19][CH2:20][CH2:21][CH2:22][O:23][C:24]4[CH:34]=[CH:33][C:27]5[CH:28]=[CH:29][C:30](=[O:32])[O:31][C:26]=5[CH:25]=4)[CH2:16][O:17][C:12]=3[CH:11]=2)C=CC=CC=1>O.CO.[Pd]>[OH:9][C:10]1[CH:36]=[CH:35][C:13]2[O:14][CH:15]([CH2:18][NH:19][CH2:20][CH2:21][CH2:22][O:23][C:24]3[CH:34]=[CH:33][C:27]4[CH:28]=[CH:29][C:30](=[O:32])[O:31][C:26]=4[CH:25]=3)[CH2:16][O:17][C:12]=2[CH:11]=1

Participants

5

Reactant 1

HCID 197786747-[3-[[(2,3-Dihydro-6-phenylmethoxy-1,4-benzodioxin-2-yl)methyl]amino]propoxy]-2H-1-benzopyran-2-one hydrochloride

Product 1

HCID 19778671HCID 19778671, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

7-[3-[[(2,3-Dihydro-6-phenylmethoxy-1,4-benzodioxin-2-yl)methyl]amino]propoxy]-2H-1-benzopyran-2-one hydrochloride (0.82 g, 1.6 mmole), prepared in Example 4 above, was dissolved in a mixture of 150 ml of water and 10 ml of methanol, 300 mg of 5% palladium on carbon added, and the mixture hydrogenated at 25 psi on a Parr apparatus for 4.5 hours. It was then filtered through celite and concentrated to dryness in vacuum. The residue was redissolved in methanol and boiled on a hot plate, the methanol being gradually replaced with isopropanol, and an additional 2.8 ml of 4N HCl/isopropanol was added. Upon cooling 0.37 g of the title compound, m.p. 244° C. (d), precipitated as a white solid, monohydrochloride.

Workup

  1. additionadded
  2. filtrationIt was then filtered through celite and
  3. concentrationconcentrated to dryness in vacuum
  4. dissolutionThe residue was redissolved in methanol
  5. additionan additional 2.8 ml of 4N HCl/isopropanol was added
  6. temperatureUpon cooling 0.37 g of the title compound, m.p. 244° C. (d)
  7. customprecipitated as a white solid, monohydrochloride

Sources & evidence

ORD record
ord-4b7b6467e6d5402c867a9a7d0e5f40a3
Source dataset
uspto-grants-1992_11
Patent number
US05166367

Reaction notes

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