3-(3-Chloropropyl)-1,3-dihydro-7,8-dimethoxy-2H-3-benzazepin-2-one → 3-(3-Chloropropyl)-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

HRID 648961Notes

Reaction equation

HRID 648961 reaction equation
[CH3:1][O:2][C:3]1[C:18]([O:19][CH3:20])=[CH:17][C:6]2[CH2:7][C:8](=[O:16])[N:9]([CH2:12][CH2:13][CH2:14][Cl:15])[CH:10]=[CH:11][C:5]=2[CH:4]=1>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[C:18]([O:19][CH3:20])=[CH:17][C:6]2[CH2:7][C:8](=[O:16])[N:9]([CH2:12][CH2:13][CH2:14][Cl:15])[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

4

Reactant 1

HCID 130925033-(3-Chloropropyl)-1,3-dihydro-7,8-dimethoxy-2H-3-benzazepin-2-one

Product 1

HCID 130925103-(3-Chloropropyl)-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Here, 1-(7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-on-3-yl)-3-chloro-propane (59.2 g, 0.2 mol) is hydrogenated in glacial acetic acid (500 ml) in the presence of 10% palladium/charcoal (5 g) for 6 hours at 50° C. and at 5 bar. The catalyst is suction filtered, the glacial acetic acid is distilled off in vacuo and after the addition of water, the residue is neutralized with potassium carbonate. The precipitate is suction filtered, washed with water until free from salt and dried.

Workup

  1. filtrationfiltered
  2. distillationthe glacial acetic acid is distilled off in vacuo
  3. additionafter the addition of water
  4. filtrationfiltered
  5. washwashed with water until free from salt
  6. customdried

Sources & evidence

ORD record
ord-a888a9b9a14547efb19d3eef9efd154d
Source dataset
uspto-grants-1988_04
Patent number
US04737495

Reaction notes

Loading…