Sodium borohydride → HCID 22903503, compound

HRID 1440269Notes

Reaction equation

HRID 1440269 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:28])[C:13]3[S:17][C:16]([NH:18][C:19](=[O:27])[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[CH3:26])=[CH:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][C:7](=O)[C:6]=2[CH:30]=1.CO.[CH3:33][NH2:34].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:28])[C:13]3[S:17][C:16]([NH:18][C:19](=[O:27])[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[CH3:26])=[CH:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH:7]([NH:34][CH3:33])[C:6]=2[CH:30]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 22903493HCID 22903493, compoundHCID 57454252Monomethylamine methanol

Product 1

HCID 22903503HCID 22903503, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 7-chloro-5-oxo-1-[5-(2-methylbenzoylamino)thenoyl]-2,3,4,5-tetrahydro-1H-benzazepine (1 g) in methanol (40 ml) are added molecular sieve 4A (2 g) and 40% methylamine methanol solution (10 ml), and the mixture is refluxed for 6 hours, and cooled. To the mixture is added with stirring sodium borohydride (0.13 g) at room temperature, and the mixture is stirred at the same temperature overnight. The reaction solution is filtered on Celite, and to the filtrate is added water, and the mixture is extracted with dichloromethane. The extract is washed with water, dried over magnesium sulfate, and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography, and recrystallized from dichloromethane-diethyl ether to give 7-chloro-5-methylamino-1-[5-(2-methylbenzoylamino)thenoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.93 g) as white powder.

Workup

  1. temperaturethe mixture is refluxed for 6 hours
  2. temperaturecooled
  3. filtrationThe reaction solution is filtered on Celite
  4. additionto the filtrate is added water
  5. extractionthe mixture is extracted with dichloromethane
  6. washThe extract is washed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated under reduced pressure
  9. customto remove the solvent
  10. customThe residue is purified by silica gel column chromatography
  11. customrecrystallized from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-6eedbfe1a9d148b093b4d786433011d6
Source dataset
uspto-grants-1996_03
Patent number
US05498609

Reaction notes

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