3-(Trifluoromethyl)aniline → 3-(Trifluoromethyl)cyclohexylamine (cis-and trans-mixture)

HRID 1580577Notes

Reaction equation

HRID 1580577 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:6][CH:7]=1.C[O-].[Na+].[H][H]>[Ru].O1CCOCC1>[F:9][C:8]([F:10])([F:11])[CH:4]1[CH2:5][CH2:6][CH2:7][CH:2]([NH2:1])[CH2:3]1

Participants

6

Reactant 3

HCID 73753-(Trifluoromethyl)anilineHCID 10942334Sodium MethoxideHCID 178418361HCID 178418361, compound

Product 1

HCID 162277663-(Trifluoromethyl)cyclohexylamine (cis-and trans-mixture)

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of 200 parts of 3-aminobenzotrifluoride, 4 parts of sodium methoxide, 15 parts of 5% ruthenium on alumina, and 200 parts of dioxane is heated in an autoclave at 175°C. under 5,000 p.s.i. of hydrogen for 4 hours. The reaction mixture is cooled and filtered and the solvent is evaporated in a rotary evaporator. The residue is distilled to give 159 parts of 3-trifluoromethylcyclohexylamine, b.p. 69°-70°/27 mm.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered
  3. customthe solvent is evaporated in a rotary evaporator
  4. distillationThe residue is distilled

Sources & evidence

ORD record
ord-469d597b28014aa2ae455cddbe8d012a
Source dataset
uspto-grants-1976_01
Patent number
US03933815

Reaction notes

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