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

HRID 2099310Notes

Reaction equation

HRID 2099310 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 with ice cooling. A solution of 823 mg (3.76 mmol) of 2-methyl-4-(trifluoromethoxy)benzamide (Example 4A) in 80 ml of THF is added dropwise and the mixture is subsequently stirred under reflux for 8 h. With ice cooling, 80 ml of 1N hydrochloric acid are added dropwise (until the evolution of gas comes to an end) and the mixture is heated under reflux for 1 h. The reaction mixture is subsequently rendered alkaline using a 1N sodium hydroxide solution and extracted three times with dichloromethane, the combined organic phases are dried over sodium sulfate and the solvent is removed in vacuo. An oil is obtained which is reacted further without further purification.

Workup

  1. custom18.8 ml (18.8 mmol) of borane-THF complex (1M) are provided under argon with ice cooling
  2. temperatureunder reflux for 8 h
  3. temperatureis heated
  4. temperatureunder reflux for 1 h
  5. extractionextracted three times with dichloromethane
  6. dry with materialthe combined organic phases are dried over sodium sulfate
  7. customthe solvent is removed in vacuo
  8. customAn oil is obtained which
  9. customis reacted further without further purification

Sources & evidence

ORD record
ord-1047f62f269a47de8cc6e8bf54ead0e1
Source dataset
uspto-grants-2009_08
Patent number
US07569563B2

Reaction notes

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