Cyclohexylamine → N-Cyclohexyl-2,2,2-trifluoroacetamide

HRID 1199283Notes

Reaction equation

[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.[CH:10]1([NH2:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>>[CH:10]1([NH:16][C:3](=[O:5])[C:2]([F:1])([F:8])[F:9])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

Reactant 2

HCID 7965Cyclohexylamine

HCID 9794Ethyl trifluoroacetate

Product 1

HCID 557702N-Cyclohexyl-2,2,2-trifluoroacetamideYield 42.1%

Conditions

Temperature: 118 °C

Procedure

In a manner similar to Example 6, ethyl trifluoroacetate (102 g, 0.72 m) was reacted with cyclohexylamine (70 g, 0.7 m). By-products/unreacted material were removed by heating the reaction mixture under increasing vacuum (final pressure 3 mm Hg) to 118° C. The pot residue was then recrystallized from hot ethyl acetate (~60 g) plus hexanes (~100 g) to yield 58 g solid which melted at 93°-95° C.

Workup

customBy-products/unreacted material were removed
temperatureby heating the reaction mixture
customThe pot residue was then recrystallized from hot ethyl acetate (~60 g) plus hexanes (~100 g)

Sources & evidence

ORD record: ord-6370105c50e34fb68cd17fb79db8725f
Source dataset: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04899249

Reaction notes

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