Trifluoroacetic acid → (4,4-Difluorocyclohexyl)amine

HRID 2221026Notes

Reaction equation

HRID 2221026 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]1

Participants

4

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

  1. customthe solvent was removed in vacuo
  2. dissolutionthe crude product was dissolved in water
  3. washwashed with chloroform
  4. additionmade basic by the addition of solid KOH
  5. extractionThe resulting mixture was extracted with CH2Cl2
  6. customdried
  7. filtrationfiltered

Sources & evidence

ORD record
ord-361391d0062a4a3c92d4cd90aa83b702
Source dataset
uspto-grants-2008_05
Patent number
US07368453B2

Reaction notes

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