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

HRID 918950Notes

Reaction equation

HRID 918950 reaction equation
[N:1]([CH:4]([C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([C:16]([F:19])([F:18])[F:17])[CH:7]=1)[CH3:5])=[N+]=[N-].[H][H]>[Pd].CO>[F:13][C:12]([F:14])([F:15])[C:10]1[CH:11]=[C:6]([CH:4]([NH2:1])[CH3:5])[CH:7]=[C:8]([C:16]([F:17])([F:18])[F:19])[CH:9]=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 crude product of 1-azido-[3,5-bis(trifluoromethyl)phenyl]ethane obtained in Example 2-5 was added with palladium-fibroin (18 mg) and methanol (6 mL), and after the atmosphere was replaced with hydrogen, the mixture was stirred at room temperature. After stirring over 1 hour, the reaction mixture was filtered through Celite, and concentrated, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol=50:1 to 5:1) to obtain 77.6 mg of α-[3,5-bis(trifluoromethyl)phenyl]ethylamine as colorless oil.

Workup

  1. stirringAfter stirring over 1 hour
  2. filtrationthe reaction mixture was filtered through Celite
  3. concentrationconcentrated
  4. customthe resulting residue was purified by silica gel column chromatography (chloroform:methanol=50:1 to 5:1)

Sources & evidence

ORD record
ord-fbd36e9fdd3a46aba1c476a3ed466ded
Source dataset
uspto-grants-2016_03
Patent number
US09272966B2

Reaction notes

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