Ammonia → HCID 20433676, compound

HRID 1154669Notes

Reaction equation

HRID 1154669 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[C:32]([O:33][CH3:34])=[CH:31][C:7]2[CH2:8][C:9](=[O:30])[N:10]([CH2:13][CH2:14][CH2:15][N:16]([CH3:29])[CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=3)[CH2:11][CH2:12][C:6]=2[CH:5]=1.[Mn]([O-])(=O)(=O)=[O:36].[K+].N>C(OC(=O)C)(=O)C.CC(C)=O>[ClH:1].[CH3:2][O:3][C:4]1[C:32]([O:33][CH3:34])=[CH:31][C:7]2[C:8](=[O:36])[C:9](=[O:30])[N:10]([CH2:13][CH2:14][CH2:15][N:16]([CH3:29])[CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=3)[CH2:11][CH2:12][C:6]=2[CH:5]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 516875Potassium PermanganateHCID 3045335Zatebradine hydrochloride

Product 1

HCID 20433676HCID 20433676, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
20 °C

Procedure

1.98 gm (4.0 mmols) 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 were suspended in 50 ml of acetic anhydride; the suspension was mixed with 2.5 gm of potassium permanganate, and the mixture was stirred for 20 minutes at 20° C. The reaction mixture was poured into ice water and made alkaline with concentrated ammonia. The precipitated manganese dioxide was suction-filtered off, and the filtrate was extracted several times with methylene chloride. The extract was dried over magnesium sulfate, evaporated in vacuo, and the residue was purified on a silica gel column with methylene chloride +1% of ethanol as the eluant. The product thus obtained was dissolved in acetone, and the hydrochloride was precipitated with ethereal hydrochloric acid.

Workup

  1. filtrationThe precipitated manganese dioxide was suction-filtered off
  2. extractionthe filtrate was extracted several times with methylene chloride
  3. dry with materialThe extract was dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customthe residue was purified on a silica gel column with methylene chloride +1% of ethanol as the eluant
  6. customThe product thus obtained
  7. customthe hydrochloride was precipitated with ethereal hydrochloric acid

Sources & evidence

ORD record
ord-4f02a53446c34883a95c8d423a6e4fea
Source dataset
uspto-grants-1984_12
Patent number
US04490369

Reaction notes

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