Trifluoroacetic acid → Piperidin-4-yl acetate

HRID 518815Notes

Reaction equation

HRID 518815 reaction equation
FC(F)(F)C(O)=O.[C:8]([O:11][CH:12]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]1)(=[O:10])[CH3:9]>ClCCl>[C:8]([O:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 21660336Tert-butyl 4-acetoxypiperidine-1-carboxylate

Product 1

HCID 11252075Piperidin-4-yl acetateYield 9.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3 ml of trifluoroacetic acid are added to a solution of 3.18 g of 2-methylpropan-2-yl 4-(acetyloxy)piperidine-1-carboxylate in 40 ml of dichloromethane, cooled to 0° C. The reaction medium is stirred for 1 hour at 0° C. and then 1 hour at ambient temperature. 5 ml of trifluoroacetic acid are added and the reaction medium is stirred for 30 minutes at ambient temperature. The reaction medium is evaporated to dryness under reduced pressure, and the resulting product is taken up with dichloromethane and an aqueous 1% NH4OH solution. The organic phase is washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and evaporated, so as to give 175 mg of piperidin-4-yl acetate in the form of a yellow oil.

Workup

  1. custom1 hour
  2. customat ambient temperature
  3. stirringthe reaction medium is stirred for 30 minutes at ambient temperature
  4. customThe reaction medium is evaporated to dryness under reduced pressure
  5. washThe organic phase is washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-4b146fa514ef4288974d0a23e806d69d
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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