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 2290216Notes

Reaction equation

HRID 2290216 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

A quantity of 59.2 gm (0.2 mol) of 1-(7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-on-3-yl)-3-chloro-propane is hydrogenated in 500 ml of glacial acetic acid in the presence of 5 gm of 10% palladium/charcoal for six hours at 50° C. under a pressure of 5 bar. The catalyst is removed by suction filtration, 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 subjected to suction filtration, washed with water until free from salt, and then dried.

Workup

  1. customThe catalyst is removed by suction filtration
  2. distillationthe glacial acetic acid is distilled off in vacuo
  3. additionafter the addition of water
  4. filtrationThe precipitate is subjected to suction filtration
  5. washwashed with water until free from salt
  6. customdried

Sources & evidence

ORD record
ord-f22c8e67d7fa44b38b311f08501a048c
Source dataset
uspto-grants-1986_10
Patent number
US04616011

Reaction notes

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