HCID 131715556, compound → HCID 131715555, compound

HRID 1253303Notes

Reaction equation

HRID 1253303 reaction equation
[ClH:1].[C:2]([O:5][C@H:6]1[C@@H:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH2:11][C:10]2[CH:21]=[C:22]([O:25]CC3C=CC=CC=3)[CH:23]=[CH:24][C:9]=2[N:8]([CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])[C:7]1=[O:38])(=[O:4])[CH3:3]>CO.[Pd]>[ClH:1].[C:2]([O:5][C@H:6]1[C@@H:12]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[CH2:11][C:10]2[CH:21]=[C:22]([OH:25])[CH:23]=[CH:24][C:9]=2[N:8]([CH2:33][CH2:34][N:35]([CH3:36])[CH3:37])[C:7]1=[O:38])(=[O:4])[CH3:3]

Participants

4

Reactant 1

HCID 131715556HCID 131715556, compound

Product 1

HCID 131715555HCID 131715555, compoundYield 102.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.5 g (0.87 mmol) of (cis)-3-(acetyloxy)-1-[2-(dimethylamino)ethyl]-1,3,4,5-tetrahydro-4-(4-methoxyphenyl)-7-(phenylmethoxy)-2H-1-benzazepin-2-one, monohydrochloride, (see Example 12) in 30 ml of methanol was treated under argon with 150 mg of 10% palladium on charcoal and shaken on the Parr hydrogenator at 50 p.s.i. for 5 hours. The catalyst was filtered off under argon, washed with methanol and the combined filtrates evaporated. The residue (which began to solidify) was rubbed under ether and the evaporation repeated. The solid was dried in vacuo for several hours yielding 0.40 g of the title compound, melting point 229°-231° C., dec., preceded by gradual sintering.

Workup

  1. filtrationThe catalyst was filtered off under argon
  2. washwashed with methanol
  3. customthe combined filtrates evaporated
  4. customthe evaporation
  5. customThe solid was dried in vacuo for several hours

Sources & evidence

ORD record
ord-76f2ed8dc9584721946dffa7f76fdd25
Source dataset
uspto-grants-1988_05
Patent number
US04748239

Reaction notes

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