Trifluoroacetic acid → 1-(Propan-2-yl)piperidin-4-amine

HRID 555355Notes

Reaction equation

HRID 555355 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH:14]([CH3:16])[CH3:15])[CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>CO>[CH:14]([N:11]1[CH2:12][CH2:13][CH:8]([NH2:7])[CH2:9][CH2:10]1)([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20801240tert-Butyl (1-isopropylpiperidin-4-yl)carbamate

Product 1

HCID 31633331-(Propan-2-yl)piperidin-4-amineYield 79.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

t-Butyl-1-isopropylpiperidin-4-ylcarbamate (2.64 g, 10.9 mmol) obtained in Preparation Example (2-iii-1) was dissolved in methanol (20 ml) in a 250 ml vessel at 0° C., and trifluoroacetic acid (TFA; 4.06 ml, 54.5 mmol, 5 eq.) was slowly added thereto while stirring. The resulting mixture was reacted for 18 hrs. After the completion of reaction, the reaction product was concentrated under reduced pressure, subjected to azeotropic distillation with CHCl3 3 times, basified with 2N aqueous KOH solution (20 ml) and extracted with CHCl3 3 times. The organic layer was separated, washed with brine, dried, filtered and distilled under reduced pressure to obtain 1.23 g of the title compound as yellow oil (yield 79.3%).

Workup

  1. customThe resulting mixture was reacted for 18 hrs
  2. customAfter the completion of reaction
  3. concentrationthe reaction product was concentrated under reduced pressure
  4. distillationsubjected to azeotropic distillation with CHCl3 3 times
  5. extractionextracted with CHCl3 3 times
  6. customThe organic layer was separated
  7. washwashed with brine
  8. customdried
  9. filtrationfiltered
  10. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-c6f04ff710fb4fcdb7d379472947382d
Source dataset
uspto-grants-2011_11
Patent number
US08053435B2

Reaction notes

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