Methylamine → HCID 19360563, compound

HRID 376901Notes

Reaction equation

HRID 376901 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[CH3:14][NH2:15].S([O-])([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:15][CH3:14])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5222694-Fluoro-3-(trifluoromethyl)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 19360563HCID 19360563, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.9 g of 4-fluoro-3-trifluoromethylbenzaldehyde, 30 ml of methylamine and 2 g of magnesium sulfate were stirred at room temperature for 2 h, the excess methylamine for the most part evaporating. The reaction mixture was diluted with ether, filtered and concentrated in vacuo. The methylbenzimine thus obtained was dissolved in 30 ml of methanol and, after addition of 2.0 g of sodium borohydride, the mixture was stirred overnight. It was concentrated in vacuo, and the residue was treated with 20 ml of 10 percent hydrochloric acid and extracted twice with tert-butyl methyl ether. The aqueous phase was then rendered alkaline and extracted twice again with tert-butyl methyl ether. After concentrating these extracts, 1.0 g of N-(4-fluoro-3-trifluoromethylbenzyl)-N-methylamine was obtained.

Workup

  1. customthe excess methylamine for the most part evaporating
  2. additionThe reaction mixture was diluted with ether
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe methylbenzimine thus obtained
  6. concentrationIt was concentrated in vacuo
  7. additionthe residue was treated with 20 ml of 10 percent hydrochloric acid
  8. extractionextracted twice with tert-butyl methyl ether
  9. extractionextracted twice again with tert-butyl methyl ether
  10. concentrationAfter concentrating these extracts

Sources & evidence

ORD record
ord-1cc0cab6e0f64ae494c8b2d66da4a993
Source dataset
uspto-grants-2000_02
Patent number
US06022899

Reaction notes

Loading…