Selenium Dioxide → HCID 20433676, compound

HRID 1154654Notes

Reaction equation

HRID 1154654 reaction equation
[Se](=O)=[O:2].[ClH:4].[CH3:5][O:6][C:7]1[C:35]([O:36][CH3:37])=[CH:34][C:10]2[CH2:11][C:12](=[O:33])[N:13]([CH2:16][CH2:17][CH2:18][N:19]([CH3:32])[CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=3)[CH2:14][CH2:15][C:9]=2[CH:8]=1>O>[ClH:4].[CH3:5][O:6][C:7]1[C:35]([O:36][CH3:37])=[CH:34][C:10]2[C:11](=[O:2])[C:12](=[O:33])[N:13]([CH2:16][CH2:17][CH2:18][N:19]([CH3:32])[CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=3)[CH2:14][CH2:15][C:9]=2[CH:8]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 3045335Zatebradine hydrochloride

Product 1

HCID 20433676HCID 20433676, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.5 gm of selenium dioxide were added to a mixture of 150 ml of diozane and 6 ml of water at 70° C.; the mixture was stirred for 15 minutes and then admixed with 3 gm of diatomaceous earth and 14.8 gm (0.03 mol) of 1-[7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl]-3-[N-methyl-N-(2-{3,4-dimethoxy-phenyl}-ethyl)-amino]-propane hydrochloride. The mixture was refluxed for 6 hours, cooled and filtered. The filtrate was evaporated in vacuo and the residue was purified on a silica gel column with methylene chloride +1% of ethanol as the eluant. The fractions were evaporated in vacuo; the residue was dissolved in acetone, and the hydrochloride was precipitated with ethereal hydrochloric acid.

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe filtrate was evaporated in vacuo
  5. customthe residue was purified on a silica gel column with methylene chloride +1% of ethanol as the eluant
  6. customThe fractions were evaporated in vacuo
  7. dissolutionthe residue was dissolved in acetone
  8. customthe hydrochloride was precipitated with ethereal hydrochloric acid

Sources & evidence

ORD record
ord-36730a7332b84a4c935a7ed36bcfc004
Source dataset
uspto-grants-1984_12
Patent number
US04490369

Reaction notes

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