Trifluoroacetic acid → (4,4-Difluorocyclohexyl)amine
Reaction equation
[F:1][C:2]1([F:16])[CH2:7][CH2:6][CH:5]([NH:8]C(OC(C)(C)C)=O)[CH2:4][CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1([F:16])[CH2:7][CH2:6][CH:5]([NH2:8])[CH2:4][CH2:3]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of N-(4,4-difluorocyclohexyl)(t-butoxy)carboxamide (6.51 mmol) in CH2Cl2 (20 mL) was treated with TFA (10 mL) at room temperature. The reaction mixture was stirred for 2 hours, the solvent was removed in vacuo, and the crude product was dissolved in water and washed with chloroform. The acidic aqueous phase was cooled at 0° C. and made basic by the addition of solid KOH. The resulting mixture was extracted with CH2Cl2, dried, and filtered yielding the title compound which was used without further purification as a 0.3 M solution in CH2Cl2.
Workup
- customthe solvent was removed in vacuo
- dissolutionthe crude product was dissolved in water
- washwashed with chloroform
- additionmade basic by the addition of solid KOH
- extractionThe resulting mixture was extracted with CH2Cl2
- customdried
- filtrationfiltered
Sources & evidence
- ORD record
- ord-c28a0b3a0e6847839697c3352feb0104
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07625909B2
Reaction notes
Loading…