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 364071Notes

Reaction equation

HRID 364071 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

Next, the 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. under 5 bar. The catalyst is removed by suction filtering, the glacial acetic acid is distilled off in vacuo and the residue is neutralized with potassium carbonate after the addition of water. The precipitate is suction filtered, washed free from salts with water and dried.

Workup

  1. customThe catalyst is removed by suction
  2. filtrationfiltering
  3. distillationthe glacial acetic acid is distilled off in vacuo
  4. additionafter the addition of water
  5. filtrationfiltered
  6. washwashed free from salts with water
  7. customdried

Sources & evidence

ORD record
ord-7d4732d370e942b288880f83794e066b
Source dataset
uspto-grants-1986_08
Patent number
US04604389

Reaction notes

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