Water → alpha-(Trifluoromethyl)benzenemethanamine

HRID 650100Notes

Reaction equation

HRID 650100 reaction equation
[F:1][C:2]([F:14])([F:13])[CH:3]([N:10]=[N+]=[N-])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[F:1][C:2]([F:13])([F:14])[CH:3]([NH2:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 5553562,2,2-Trifluoro-1-phenylethyl azideHCID 21226445Aluminium lithium hydride

Product 1

HCID 89166alpha-(Trifluoromethyl)benzenemethanamineYield 88%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of α-(trifluoromethyl)benzylazide (849 mf, 4.22 mmol) in ether (10 mL), lithium aluminum hydride (160 mg, 12.7 mmol) was added. The reaction mixture was stirred at room temerature for 2 hours. Then 0.46 ml H2O, 0.51 mL of 15% NaOH and 1.06 mL of H2O were added. The solid was filtered. The liquid was concentrated under reduced pressure to give desired product (647 mg, 88%). EI-MS m/z 176 (M+).

Workup

  1. filtrationThe solid was filtered
  2. concentrationThe liquid was concentrated under reduced pressure

Sources & evidence

ORD record
ord-50066a2848564cf4ae3bce8b162835ee
Source dataset
uspto-grants-2001_08
Patent number
US06271261B1

Reaction notes

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