Piperidinium acetate → HCID 178495009, compound

HRID 1620749Notes

Reaction equation

HRID 1620749 reaction equation
[CH3:1][O:2][C:3]([CH3:18])([CH3:17])[C@@H:4]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[NH:5][C:6]1[CH2:10][S:9][C:8](=[O:11])[N:7]=1.[F:19][C:20]([F:41])([F:40])[C:21]1[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[CH:32][C:22]=1[CH2:23][N:24]1[CH2:29][CH2:28][CH:27]([CH:30]=O)[CH2:26][CH2:25]1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:41][C:20]([F:19])([F:40])[C:21]1[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[CH:32][C:22]=1[CH2:23][N:24]1[CH2:29][CH2:28][CH:27](/[CH:30]=[C:10]2/[C:6]([NH:5][C@H:4]([C:12]([N:14]([CH3:15])[CH3:16])=[O:13])[C:3]([O:2][CH3:1])([CH3:18])[CH3:17])=[N:7][C:8](=[O:11])[S:9]/2)[CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 3014295Piperidinium acetateHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178495010HCID 178495010, compound

Product 1

HCID 178495009HCID 178495009, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-methoxy-N,N-dimethyl-N2-(2-oxo-2,5-dihydro-1,3-thiazol-4-yl)-L-valinamide (460 mg) and 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (628 mg) in 2-propanol (15 mL) was added piperidinium acetate (269 mg) at room temperature. The reaction mixture was stirred at 60° C. for 3 hr, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) and recrystallized from ethyl acetate/heptane to give the title compound (380 mg).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  3. customrecrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-f6dc2403625d410e9cca637ec1786281
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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