1-[3,5-Bis(trifluoromethyl)phenyl]ethyl azide → 3,5-Bis(trifluoromethyl)-alpha-methylbenzylamine

HRID 1399515Notes

Reaction equation

HRID 1399515 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([CH:13]([N:15]=[N+]=[N-])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[H][H]>CO.[Pd]>[F:1][C:2]([F:18])([F:19])[C:3]1[CH:4]=[C:5]([CH:13]([NH2:15])[CH3:14])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

5

Reactant 2

HCID 727612691-[3,5-Bis(trifluoromethyl)phenyl]ethyl azideHCID 178418361HCID 178418361, compound

Product 1

HCID 27822323,5-Bis(trifluoromethyl)-alpha-methylbenzylamineYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The resulting 1-[3,5-bis(trifluoromethyl)phenyl]ethyl azide (crude product: 111.5 mg) was dissolved in methanol (6 mL) and the solution was added with palladium-fibroin (18 mg) for hydrogen substitution, and then the mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered through Celite, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol=50:1 to 5:1) to obtain 77.6 mg of 1-[3,5-bis(trifluoromethyl)phenyl]ethylamine as colorless oil (yield: 91%, for 2 steps).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (chloroform:methanol=50:1 to 5:1)

Sources & evidence

ORD record
ord-6b01d7b85ebc4644bade8e709ebd9816
Source dataset
uspto-grants-2014_12
Patent number
US08906895B2

Reaction notes

Loading…