1-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde → HCID 178459113, compound

HRID 1620595Notes

Reaction equation

HRID 1620595 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.[OH:24][C:25]([CH3:37])([CH3:36])[C:26]#[C:27][CH2:28][NH:29][C:30]1[CH2:34][S:33][C:32](=[O:35])[N:31]=1>CC(O)C.C([O-])(=O)C.[NH2+]1CCCCC1>[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:34]2/[C:30]([NH:29][CH2:28][C:27]#[C:26][C:25]([OH:24])([CH3:37])[CH3:36])=[N:31][C:32](=[O:35])[S:33]/2)[CH2:8][CH2:7]1

Participants

5

Reactant 2

HCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178459112HCID 178459112, compound

Product 1

HCID 178459113HCID 178459113, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolvent2×HCID 3014295Piperidinium acetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (400 mg) in 2-propanol (10 mL) were added a solution of 4-[(4-hydroxy-4-methylpent-2-yn-1-yl)amino]-1,3-thiazol-2(5H)-one (365 mg) in 2-propanol (5 mL) and piperidinium acetate (175 mg). The reaction mixture was stirred at 60° C. overnight and concentrated. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was 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) to give the title compound (540 mg).

Workup

  1. concentrationconcentrated
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed 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)

Sources & evidence

ORD record
ord-779a654f344e4a8198131c5e890bf18e
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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