Piperidinium acetate → HCID 178518135, compound

HRID 1620617Notes

Reaction equation

HRID 1620617 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.[O:24]=[C:25]1[CH2:29][CH2:28][CH2:27][N:26]1[CH2:30][CH2:31][CH2:32][NH:33][C:34]1[CH2:38][S:37][C:36](=[O:39])[N:35]=1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(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:38]2/[C:34]([NH:33][CH2:32][CH2:31][CH2:30][N:26]3[CH2:27][CH2:28][CH2:29][C:25]3=[O:24])=[N:35][C:36](=[O:39])[S:37]/2)[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 3014295Piperidinium acetateHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178518136HCID 178518136, compound

Product 1

HCID 178518135HCID 178518135, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (500 mg) in 2-propanol (10 mL) were added 4-([3-(2-oxopyrrolidin-1-yl)propyl]amino)thiazol-2(5H)-one (866 mg) and piperidinium acetate (107 mg). The reaction mixture was stirred at 60° C. overnight, 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 (439 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-386e2a64bb834727b85ecf9ec3b33978
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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