Sodium Bicarbonate → HCID 19891053, compound

HRID 893723Notes

Reaction equation

HRID 893723 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[O:7][CH2:8][CH2:9][CH2:10][NH:11][CH2:12][CH:13]1[O:18][C:17]2[CH:19]=[CH:20][CH:21]=[C:22]([O:23]C)[C:16]=2[O:15][CH2:14]1.C(=O)(O)[O-].[Na+]>Br.O>[NH2:3][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[O:7][CH2:8][CH2:9][CH2:10][NH:11][CH2:12][CH:13]1[O:18][C:17]2[CH:19]=[CH:20][CH:21]=[C:22]([OH:23])[C:16]=2[O:15][CH2:14]1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 19891059HCID 19891059, compound

Product 1

HCID 19891053HCID 19891053, compoundYield 52.6%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

N-[3-(3-Aminophenoxy)propyl]-2,3-dihydro-5-methoxy-1,4-benzodioxin-2-methanamine dihydrochloride quarter hydrate (0.79 g, 1.9 mmole), prepared in Example 2 above, was dissolved in 26.5 ml of 48% HBr and refluxed under nitrogen for 23 hours. Upon cooling, the mixture was diluted to 250 ml with water and carefully neutralized with solid sodium bicarbonate. It was then extracted with two 200 ml portions of 3:1 dichloromethane/isopropanol and the combined extracts were washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and concentrated to dryness in vacuum. The residue was column chromatographed on silica gel using 5% methanol/dichloromethane to which 1 ml/liter aqueous ammonia had been added. The product-containing fractions were combined, concentrated in vacuum, and the residue crystallized from 20 ml of isopropanol with the addition of 4 ml 4N HCl/isopropanol to give 0.33 g of the title compound (m.p. 183°-190° C.) as a beige solid, dihydrochloride.

Workup

  1. temperaturerefluxed under nitrogen for 23 hours
  2. temperatureUpon cooling
  3. extractionIt was then extracted with two 200 ml portions of 3:1 dichloromethane/isopropanol
  4. washthe combined extracts were washed with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness in vacuum
  8. customchromatographed on silica gel using 5% methanol/dichloromethane to which 1 ml/liter aqueous ammonia
  9. additionhad been added
  10. concentrationconcentrated in vacuum
  11. customthe residue crystallized from 20 ml of isopropanol with the addition of 4 ml 4N HCl/isopropanol

Sources & evidence

ORD record
ord-d1d1c71199f245039947611b49d2653e
Source dataset
uspto-grants-1992_06
Patent number
US05126366

Reaction notes

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