1,3-Dihydro-7,8-dimethoxy-2H-3-benzazepin-2-one → 3-[(N-Benzyl-piperidin-3-yl)-methyl]-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one

HRID 1681991Notes

Reaction equation

HRID 1681991 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][CH:10]=[CH:11][C:5]=2[CH:4]=1.CC(C)([O-])C.[K+].[CH2:23]([N:30]1[CH2:35][CH2:34][CH2:33][CH:32]([CH2:36]Br)[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CS(C)=O>[CH2:23]([N:30]1[CH2:35][CH2:34][CH2:33][CH:32]([CH2:36][N:9]2[C:8](=[O:12])[CH2:7][C:6]3[CH:13]=[C:14]([O:15][CH3:16])[C:3]([O:2][CH3:1])=[CH:4][C:5]=3[CH:11]=[CH:10]2)[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 14823731,3-Dihydro-7,8-dimethoxy-2H-3-benzazepin-2-oneHCID 190759011-Benzyl-3-(bromomethyl)piperidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 198035973-[(N-Benzyl-piperidin-3-yl)-methyl]-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

17.54 g (0.08 mol) of 7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one are suspended in 150 ml of dimethylsulphoxide and 8.98 g (0.08 mol) of potassium tert.butoxide are added with stirring. After 45 minutes, 21.45 g (0.08 mol) of N-benzyl-3-(bromomethyl)-piperidine dissolved in 50 ml of dimethylsulphoxide are added dropwize to the resulting solution with stirring. After 2 hours the mixture is poured onto ice water. The aqueous phase is extracted three times, each time with 150 ml of ethyl acetate. The combined organic phases are washed with water, dried over magnesium sulphate, concentrated by evaporation in vacuo and purified over 800 g of aluminium oxide (neutral, activity II-III) with methylene chloride and then with increasing amounts of ethanol (up to 3%). Yield: 14.3 g (44% of theory), Rf value: 0.35 (aluminium oxide neutral, eluant: 1% ethanol in methylene chloride).

Workup

  1. additionare added dropwize to the resulting solution
  2. stirringwith stirring
  3. additionAfter 2 hours the mixture is poured onto ice water
  4. extractionThe aqueous phase is extracted three times
  5. washThe combined organic phases are washed with water
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated by evaporation in vacuo
  8. custompurified over 800 g of aluminium oxide (neutral, activity II-III) with methylene chloride

Sources & evidence

ORD record
ord-bba51b87378f4483b67d67964452067c
Source dataset
uspto-grants-1992_12
Patent number
US05175157

Reaction notes

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