1,3-Dihydro-7,8-dimethoxy-2H-3-benzazepin-2-one → HCID 54168333, compound

HRID 1681999Notes

Reaction equation

HRID 1681999 reaction equation
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[C:20]([O:21][CH3:22])=[CH:19][C:12]2[CH2:13][C:14](=[O:18])[NH:15][CH:16]=[CH:17][C:11]=2[CH:10]=1.[CH2:23]([N:30]1[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]([CH2:37]Br)[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CS(C)=O.C(OCC)(=O)C>[CH2:23]([N:30]1[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]([CH2:37][N:15]2[C:14](=[O:18])[CH2:13][C:12]3[CH:19]=[C:20]([O:21][CH3:22])[C:9]([O:8][CH3:7])=[CH:10][C:11]=3[CH:17]=[CH:16]2)[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 14823731,3-Dihydro-7,8-dimethoxy-2H-3-benzazepin-2-oneHCID 19803730HCID 19803730, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 54168333HCID 54168333, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.3 g (0.02 mol) of potassium tert.butoxide are added to a solution of 4.4 g (0.02 mol) of 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one in 100ml of absolute dimethylsulphoxide. After stirring for 30 minutes at ambient temperature, 5.6 g (0.020 mol) of 1-benzyl-3-bromomethyl-hexahydro-azepine are added and the resulting mixture is stirred for 2 hours at ambient temperature. The reaction mixture is dissolved in ethyl acetate and extracted several times with water. The organic phase is dried over magnesium sulphate and evaporated down in vacuo. The residue is purified by column chromatography over aluminium oxide N (activity II, eluant: methylene chloride, methylene chloride+0.3% ethanol). Yield: 4.2 g (50% of theory), IR spectrum (methylene chloride): 1655 cm-1 (CO).

Workup

  1. stirringthe resulting mixture is stirred for 2 hours at ambient temperature
  2. extractionextracted several times with water
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. customevaporated down in vacuo
  5. customThe residue is purified by column chromatography over aluminium oxide N (activity II, eluant: methylene chloride, methylene chloride+0.3% ethanol)

Sources & evidence

ORD record
ord-34c9f8524f4744689cf45beb62c38603
Source dataset
uspto-grants-1992_12
Patent number
US05175157

Reaction notes

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