HCID 178418361, compound → HCID 178480857, compound

HRID 2397532Notes

Reaction equation

HRID 2397532 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[N:12]=[C:11]([NH:13][CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22]CC4C=CC=CC=4)=[C:18]([O:30]CC4C=CC=CC=4)[CH:17]=3)[CH2:10][N:9]([CH3:38])[C:8](=[O:39])[C:7]=2[CH:40]=1.[H][H]>[Pd].CO>[ClH:2].[OH:30][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=1[OH:22])[CH2:15][CH2:14][NH:13][C:11]1[CH2:10][N:9]([CH3:38])[C:8](=[O:39])[C:7]2[CH:40]=[CH:3][CH:4]=[CH:5][C:6]=2[N:12]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178480856HCID 178480856, compound

Product 1

HCID 178480857HCID 178480857, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 11.34 g (0.0197 m) of 7-chloro-2-(3,4-dibenzyloxyphenethylamino)-3,4-dihydro-4-methyl-5H-1,4-benzodiazepine-5-one hydrochloride and 10% palladium on charcoal catalyst in 250 ml of absolute methanol is hydrogenated until no more hydrogen is absorbed. The catalyst is removed by filtration and the filtrate is concentrated to dryness in vacuo to give crude 3,4-dihydro-2-(3,4-dihydroxyphenethylamino)-4-methyl-5H-1,4-benzodiazepine-5-one hydrochloride hemi methanolate. Several recrystallizations from ethanol/ether give the pure product, m.p. 179°-180° C. dec.

Workup

  1. customis absorbed
  2. customThe catalyst is removed by filtration
  3. concentrationthe filtrate is concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-ff8fea96bc894426864828bd05ebf7e3
Source dataset
uspto-grants-1977_05
Patent number
US04022767

Reaction notes

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