Water → 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-dihydrochloride

HRID 1154676Notes

Reaction equation

HRID 1154676 reaction equation
[CH3:1][O:2][C:3]1[C:14]([O:15][CH3:16])=[CH:13][C:6]2[CH2:7][C:8](=[O:12])[NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.[Cl:17][CH2:18][CH2:19][CH2:20][N:21]([CH3:34])[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=1.O>CS(C)=O>[ClH:17].[ClH:17].[CH3:1][O:2][C:3]1[C:14]([O:15][CH3:16])=[CH:13][C:6]2[CH2:7][C:8](=[O:12])[N:9]([CH2:18][CH2:19][CH2:20][N:21]([CH3:34])[CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=3)[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 577693N-(3-Chloropropyl)-3,4-dimethoxy-N-methylphenethylamineHCID 114017697,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one

Product 1

HCID 204336851-[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-dihydrochloride

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1.1 gm (5.0 mmols) of 7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one were suspended in 20 ml of dimethyl sulfoxide, and the suspension was mixed with 0.6 gm (5.3 mmols) of potassium tert. butylate while stirring. After 10 minutes, the solution was mixed with 2.0 gm (7.4 mmols) of 1-chloro-3-[N-methyl-N-(2-{3,4-dimethoxy-phenyl}-ethyl)-amino]-propane; the mixture was stirred for one hour at 50° C. and then poured into water; the aqueous mixture was extracted with ethyl acetate, and the organic phase was evaporated in vacuo. The residue was purified on silica gel with methylene chloride +10% of methanol as the eluant, and the dihydrochloride was precipitated from acetone with ethereal hydrochloric acid.

Workup

  1. stirringthe mixture was stirred for one hour at 50° C.
  2. extractionthe aqueous mixture was extracted with ethyl acetate
  3. customthe organic phase was evaporated in vacuo
  4. customThe residue was purified on silica gel with methylene chloride +10% of methanol as the eluant
  5. customthe dihydrochloride was precipitated from acetone with ethereal hydrochloric acid

Sources & evidence

ORD record
ord-ad6624aec3ba45f5bf0598f0c6d817dc
Source dataset
uspto-grants-1984_12
Patent number
US04490369

Reaction notes

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