Water → 1H-1,4-Benzodiazepin-9-amine, 2,3,4,5-tetrahydro-3-methyl-, (S)-

HRID 1082055Notes

Reaction equation

HRID 1082055 reaction equation
[NH2:1][C:2]1[C:12]2[NH:11][C:10](=O)[C@H:9]([CH3:14])[NH:8][C:7](=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCOCC1>[CH3:14][C@@H:9]1[NH:8][CH2:7][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([NH2:1])[C:12]=2[NH:11][CH2:10]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 11095747HCID 11095747, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 118299831H-1,4-Benzodiazepin-9-amine, 2,3,4,5-tetrahydro-3-methyl-, (S)-Yield 99.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

14.8 g (0.072 mol) of (S)-9-amino-3-methyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione in 455 ml of dioxane are heated at the reflux temperature with stirring for 48 hours in the presence of 17 g of lithium aluminium hydride. The reaction mixture is cooled in an ice bath and then, slowly and successively, 17 ml of water, 17 ml of a 5N sodium hydroxide solution and 45 ml of water are added. The mixture is left stirring for 2 hours at room temperature, filtration is carried out and washing is carried out with hot tetrahydrofuran and with dichloromethane. The organic phase is recovered and is concentrated. There are obtained 12.7 g of product which is used as is in the following stage.

Workup

  1. temperatureThe reaction mixture is cooled in an ice bath
  2. waitThe mixture is left
  3. filtrationfiltration
  4. washwashing
  5. customThe organic phase is recovered
  6. concentrationis concentrated

Sources & evidence

ORD record
ord-f85504502baf461f9da5886cb89b7173
Source dataset
uspto-grants-1996_12
Patent number
US05589476

Reaction notes

Loading…