Sodium Carbonate → HCID 86739859, compound

HRID 1154686Notes

Reaction equation

HRID 1154686 reaction equation
[CH3:1][O:2][C:3]1[C:32]([O:33][CH3:34])=[CH:31][C:6]2[C:7](=O)[C:8](=[O:29])[N:9]([CH2:12][CH2:13][CH2:14][N:15]([CH3:28])[CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=3)[CH2:10][CH2:11][C:5]=2[CH:4]=1.[ClH:35].[NH2:36][OH:37].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.CC(C)=O>[ClH:35].[N:36](=[C:7]1[C:6]2[CH:31]=[C:32]([O:33][CH3:34])[C:3]([O:2][CH3:1])=[CH:4][C:5]=2[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][N:15]([CH3:28])[CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=2)[C:8]1=[O:29])[OH:37]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 20433677HCID 20433677, compound

Product 1

HCID 86739859HCID 86739859, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

A mixture of 3.6 gm of (6.8 mmols) of 1-[7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-1,2-dion-3-yl]-3-[N-methyl-N-(2-{3,4-dimethoxy-phenyl}-ethyl)-amino]-propane, 0.57 gm of hydroxylamine hydrochloride and 0.87 gm of sodium carbonate was refluxed for 8 hours in 100 ml of ethanol. The solvent was then distilled off in vacuo; the residue was dissolved in water/methylene chloride, and the organic phase was separated, dried over magnesium sulfate and concentrated by evaporation. The residue was purified on silica gel, using methylene chloride and 5% ethanol as the eluant. The free base product thus obtained was dissolved in acetone, and the hydrochloride was precipitated by the addition of ethereal hydrochloric acid.

Workup

  1. distillationThe solvent was then distilled off in vacuo
  2. dissolutionthe residue was dissolved in water/methylene chloride
  3. customthe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe residue was purified on silica gel
  7. customThe free base product thus obtained
  8. customthe hydrochloride was precipitated by the addition of ethereal hydrochloric acid

Sources & evidence

ORD record
ord-90343e3b928349a686f030ea472a3808
Source dataset
uspto-grants-1984_12
Patent number
US04490369

Reaction notes

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