Potassium tert-butoxide → HCID 178456914, compound

HRID 1620478Notes

Reaction equation

HRID 1620478 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH:12]=O)[CH2:8][CH2:7]1.[CH2:24]([NH:27][C:28]1[CH2:32][S:31][C:30](=[O:33])[N:29]=1)[C:25]#[CH:26].CC(C)([O-])C.[K+]>C(O)C>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9](/[CH:12]=[C:32]2/[C:28]([NH:27][CH2:24][C:25]#[CH:26])=[N:29][C:30](=[O:33])[S:31]/2)[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178456890HCID 178456890, compound

Product 1

HCID 178456914HCID 178456914, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (15 g) and 4-(prop-2-yn-1-ylamino)-1,3-thiazol-2(5H)-one (8.18 g) in ethanol (150 mL) was added potassium tert-butoxide (5.95 g), and the reaction mixture was stirred at 80° C. for 30 min. The reaction mixture was concentrated, saturated aqueous ammonium chloride solution/ethyl acetate were added to the residue, and the organic layer was separated, washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), and the residue was washed with diisopropyl ether to give the title compound (9.96 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionsaturated aqueous ammonium chloride solution/ethyl acetate were added to the residue
  3. customthe organic layer was separated
  4. washwashed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  8. washthe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-8dfc4a285f7d4befbd764aec0438a911
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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