Trifluoroacetic acid → (Piperidin-4-yl)(thiophen-2-yl)methanone

HRID 1598774Notes

Reaction equation

HRID 1598774 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([CH:8]1[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]1)=[O:7].FC(F)(F)C(O)=O>C(OCC)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([CH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1)=[O:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15337452Tert-butyl 4-(thiophene-2-carbonyl)piperidine-1-carboxylate

Product 1

HCID 15337453(Piperidin-4-yl)(thiophen-2-yl)methanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Mix 4-[(thiophene-2-yl)carbonyl]-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester (12.9 g, 43.67 mmol) and trifluoroacetic acid (80 mL) and stir at room temperature for 2 hours. Cool in an ice/water bath and dilute with ethyl ether. Collect the resulting solid by filtration, wash with ethyl acetate and recrystallize (methanol/ethyl ether) to give the title compound as an off-white solid; mp 186°-187° C.

Workup

  1. temperatureCool in an ice/water bath
  2. customCollect the resulting solid
  3. filtrationby filtration
  4. washwash with ethyl acetate
  5. customrecrystallize (methanol/ethyl ether)

Sources & evidence

ORD record
ord-4810d2772701441b87864a626c281b16
Source dataset
uspto-grants-1998_04
Patent number
US05739150

Reaction notes

Loading…