Piperidine → Ethyl 2-(1-piperidinyl)-4-(trifluoromethyl)oxazole-5-carboxylate

HRID 1020338Notes

Reaction equation

HRID 1020338 reaction equation
Br[C:2]1[O:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>FC(F)(F)C1C=CC=CC=1.CCOC(C)=O>[N:16]1([C:2]2[O:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 8082PiperidineHCID 53403202Ethyl 2-bromo-4-(trifluoromethyl)-1,3-oxazole-5-carboxylate

Product 1

HCID 57461777Ethyl 2-(1-piperidinyl)-4-(trifluoromethyl)oxazole-5-carboxylateYield 88%

Reagents, catalysts & solvents 2

HCID 7368(Trifluoromethyl)benzeneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of ethyl 2-bromo-4-trifluoromethyloxazole-5-carboxylate (A-2) (0.85 mL) in α,α,α-trifluorotoluene (10 mL) at RT was added piperidine (1.1 mL). The reaction mixture was heated at 120° C. for 20 min by microwave then cooled to RT and diluted with EtOAc (100 mL). The organic solution was washed with H2O (2×100 mL), saturated NH4Cl (1×100 mL), brine (1×100 mL), dried over Na2SO4, filtered, and concentrated to give ethyl 2-(1-piperidinyl)-4-trifluoromethyloxazole-5-carboxylate (A-3) as a yellow solid (1.28 g, 88% yield). LCMS (ESI) calcd for [M+1]+ 293.1. found 293.2.

Workup

  1. temperaturethen cooled to RT
  2. washThe organic solution was washed with H2O (2×100 mL), saturated NH4Cl (1×100 mL), brine (1×100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3a86139f1b314bf087441ef6d04e3098
Source dataset
uspto-grants-2014_05
Patent number
US08716312B2

Reaction notes

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