Hydrochloric Acid → 2-Methyl-4-(trifluoromethoxy)benzylamine

HRID 251854Notes

Reaction equation

HRID 251854 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=O.Cl.[OH-].[Na+]>C1COCC1>[CH3:1][C:2]1[CH:10]=[C:9]([O:11][C:12]([F:13])([F:14])[F:15])[CH:8]=[CH:7][C:3]=1[CH2:4][NH2:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 27755492-Methyl-4-(trifluoromethoxy)benzamide

Product 1

HCID 577941232-Methyl-4-(trifluoromethoxy)benzylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

18.8 ml (18.8 mmol) of borane-THF-complex (1M) are provided under argon and ice cooling. A solution of 823 mg (3.76 mmol) of 2-methyl-4-(trifluoromethoxy)benzamide (Example 68A) in 80 ml of THF is added dropwise and the reaction mixture is subsequently stirred for 8 h under reflux. Under ice cooling 80 ml of 1N hydrochloric acid are added dropwise (until the end of the evolution of gas) and the reaction mixture is heated for 1 h under reflux. The reaction mixture is subsequently adjusted to an alkaline pH with a 1N sodium hydroxide solution, extracted three times with dichloromethane and the combined organic phases are dried over sodium sulfate and the solvent is removed under vacuum. An oil is obtained which is reacted further without further purification. Yield: 732 mg (95% of theory).

Workup

  1. temperatureunder reflux
  2. temperatureis heated for 1 h
  3. temperatureunder reflux
  4. extractionextracted three times with dichloromethane
  5. dry with materialthe combined organic phases are dried over sodium sulfate
  6. customthe solvent is removed under vacuum
  7. customAn oil is obtained which
  8. customis reacted further without further purification

Sources & evidence

ORD record
ord-d408efcf53a8454bb79e0a2157ff88b8
Source dataset
uspto-grants-2011_01
Patent number
US07867992B2

Reaction notes

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