3-[(N-Benzyl-piperidin-3-yl)-methyl]-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one → 3-[(piperidin-3-yl)-methyl]-7,8-dimethoxy1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

HRID 1681992Notes

Reaction equation

HRID 1681992 reaction equation
C([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][N:15]2[C:21](=[O:22])[CH2:20][C:19]3[CH:23]=[C:24]([O:29][CH3:30])[C:25]([O:27][CH3:28])=[CH:26][C:18]=3[CH:17]=[CH:16]2)[CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)(=O)C.[Pd]>[NH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][N:15]2[C:21](=[O:22])[CH2:20][C:19]3[CH:23]=[C:24]([O:29][CH3:30])[C:25]([O:27][CH3:28])=[CH:26][C:18]=3[CH2:17][CH2:16]2)[CH2:9]1

Participants

5

Reactant 2

HCID 198035973-[(N-Benzyl-piperidin-3-yl)-methyl]-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 198038413-[(piperidin-3-yl)-methyl]-7,8-dimethoxy1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

14.3 g (0.0352 mol) of 3-[(N-benzyl-piperidin-3-yl)-methyl]7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one are hydrogenated in 120 ml of glacial acetic acid in the presence of 1.5 g of 10% palladium/charcoal for 4 hours at 50° C. under 5 bar of hydrogen. The catalyst is then removed by suction filtering, the glacial acetic acid is distilled off in vacuo and, after the addition of water, the residue is neutralized with potassium carbonate. The greasy precipitate is extracted with methylene chloride, the organic phase is dried over magnesium sulphate and concentrated by evaporation in vacuo. Yield: 9.3 g (83% of theory), Melting point: 152°-156° C.

Workup

  1. customThe catalyst is then removed by suction
  2. filtrationfiltering
  3. distillationthe glacial acetic acid is distilled off in vacuo
  4. additionafter the addition of water
  5. extractionThe greasy precipitate is extracted with methylene chloride
  6. dry with materialthe organic phase is dried over magnesium sulphate
  7. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-af6294ce9d014e88b761a59cf89d65d0
Source dataset
uspto-grants-1992_12
Patent number
US05175157

Reaction notes

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