Sodium Carbonate → HCID 19891060, compound

HRID 893724Notes

Reaction equation

HRID 893724 reaction equation
O.Cl.Cl.[NH2:4][C:5]1[CH:6]=[C:7]([CH:26]=[CH:27][CH:28]=1)[O:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH:14]1[O:19][C:18]2[C:20]([O:24]C)=[CH:21][CH:22]=[CH:23][C:17]=2[O:16][CH2:15]1.C(=O)([O-])[O-].[Na+].[Na+]>Br.O>[NH2:4][C:5]1[CH:6]=[C:7]([CH:26]=[CH:27][CH:28]=1)[O:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH:14]1[O:19][C:18]2[C:20]([OH:24])=[CH:21][CH:22]=[CH:23][C:17]=2[O:16][CH2:15]1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 19891045HCID 19891045, compound

Product 1

HCID 19891060HCID 19891060, compoundYield 40.7%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

N-[3-(3-Aminophenoxy)propyl]-2,3-dihydro-8-methoxy-1,4-benzodioxin-2-methanamine dihydrochloride hydrate (1.2 g, 2.75 mmole), prepared in Example 11 above, was dissolved in 25 ml of 48% HBr and refluxed overnight under nitrogen. The mixture was diluted with water to 300 ml, carefully neutralized with solid sodium carbonate, and twice extracted with 200 ml of 3:1 dichloromethane/isopropanol. The combined extracts were washed with saturated aqueous sodium chloride, dried over sodium sulfate, filtered and concentrated in vacuum. The residue was crystallized from 50 ml of isopropanol with the addition of 2 ml of 4N HCl/isopropanol to give 0.37 g of the title compound as a tan solid, dihydrochloride, quarter hydrate, m.p. 249°-255° C.

Workup

  1. temperaturerefluxed overnight under nitrogen
  2. extractiontwice extracted with 200 ml of 3:1 dichloromethane/isopropanol
  3. washThe combined extracts were washed with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customThe residue was crystallized from 50 ml of isopropanol with the addition of 2 ml of 4N HCl/isopropanol

Sources & evidence

ORD record
ord-ac2b5c67bb744f5d83b4331cf2f5ee51
Source dataset
uspto-grants-1992_06
Patent number
US05126366

Reaction notes

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