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 2082460Notes

Reaction equation

HRID 2082460 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-389711f351c9458a86af526b9df0b29f
Source dataset
uspto-grants-1993_02
Patent number
US05189171

Reaction notes

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