Hydrochloric Acid → 3,5-Bis(trifluoromethyl)benzylamine

HRID 2270456Notes

Reaction equation

HRID 2270456 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[CH:6]=[N:7]O.Cl.[H][H].[OH-].[Na+]>CO.[Pd].CCOCC>[F:1][C:2]([F:16])([F:17])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:13])[F:14])[CH:11]=1)[CH2:6][NH2:7]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 27263643,5-Bis-trifluoromethyl-benzaldehyde oximeHCID 178418361HCID 178418361, compound

Product 1

HCID 5210993,5-Bis(trifluoromethyl)benzylamineYield 94.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

The second step of the process of the present invention was conducted as follows. At first, 5.03 g (19.6 mol) of 3,5-bis(trifluoromethyl)benzaldehyde oxime were dissolved in methanol followed by the addition of 3.0 g (82.3 mmol) of hydrogen chloride gas and 252 mg of a catalyst (i.e., activated carbon carrying thereon 5% palladium) and stirring for 5.5 hours in a hydrogen atmosphere at 10 atm and room temperature (approx. 25° C.). After removing the catalyst, ether was added to the reaction liquid, and the reaction liquid was neutralized with aqueous sodium hydroxide solution. As a result of analyzing the separated ether layer by gas chromatography, 3,5-bis(trifluoromethyl)benzylamine was formed at a yield of 94.2%.

Workup

  1. customAfter removing the catalyst, ether
  2. additionwas added to the reaction liquid
  3. customthe reaction liquid
  4. customAs a result

Sources & evidence

ORD record
ord-ad96e52346564eaab6af024ad26d6aef
Source dataset
uspto-grants-2001_12
Patent number
US06331649B1

Reaction notes

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