Piperidinium acetate → HCID 178480331, compound

HRID 1620754Notes

Reaction equation

HRID 1620754 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9]2[CH2:13][S:12][C:11](=[O:14])[N:10]=2)[C:3]1=[O:15].[F:16][C:17]([F:38])([F:37])[C:18]1[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:19]=1[CH2:20][N:21]1[CH2:26][CH2:25][CH:24]([CH:27]=O)[CH2:23][CH2:22]1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:38][C:17]([F:16])([F:37])[C:18]1[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:19]=1[CH2:20][N:21]1[CH2:26][CH2:25][CH:24](/[CH:27]=[C:13]2/[C:9]([NH:8][CH:4]3[CH2:5][CH2:6][CH2:7][N:2]([CH3:1])[C:3]3=[O:15])=[N:10][C:11](=[O:14])[S:12]/2)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 3014295Piperidinium acetateHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178480330HCID 178480330, compound

Product 1

HCID 178480331HCID 178480331, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-methyl-3-[(2-oxo-2,5-dihydro-1,3-thiazol-4-yl)amino]piperidin-2-one (220 mg) and 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (339 mg) in 2-propanol (5 mL) was added piperidinium acetate (141 mg) at room temperature. 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 (NH, ethyl acetate/hexane) and recrystallized from ethyl acetate/heptane to give the title compound (158 mg).

Workup

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

Sources & evidence

ORD record
ord-d92761f283644aeab913efaf050d3152
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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