Trifluoroacetic acid → 3-(3-Cyclopropyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidine

HRID 1642849Notes

Reaction equation

HRID 1642849 reaction equation
[CH:1]1([C:4]2[N:8]=[C:7]([CH:9]3[CH2:14][CH:13]([C:15]4[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=4)[CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]3)[O:6][N:5]=2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([C:4]2[N:8]=[C:7]([CH:9]3[CH2:14][CH:13]([C:15]4[CH:16]=[CH:17][C:18]([C:21]([F:22])([F:24])[F:23])=[CH:19][CH:20]=4)[CH2:12][NH:11][CH2:10]3)[O:6][N:5]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58002290tert-Butyl 3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidine-1-carboxylate

Product 1

HCID 580025193-(3-Cyclopropyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.23 g (7.38 mmol) of the compound from Example 182A were initially charged in 60 ml of dichloromethane and, at RT, reacted with 5.7 ml (8.42 g, 73.8 mmol) of trifluoroacetic acid. The reaction mixture was stirred at RT for 16 h and then concentrated under reduced pressure. The residue was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulphate, filtered and concentrated under reduced pressure. Yield: 2.48 g (92% of theory)

Workup

  1. concentrationconcentrated under reduced pressure
  2. washwashed with saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-05c579d739d14714ae6aaefa60e7e789
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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