Piperidinium acetate → HCID 178518153, compound

HRID 1620722Notes

Reaction equation

HRID 1620722 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[CH2:9][S:8][C:7](=[O:10])[N:6]=1.[F:11][C:12]([F:33])([F:32])[C:13]1[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:14]=1[CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([CH:22]=O)[CH2:18][CH2:17]1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:33][C:12]([F:11])([F:32])[C:13]1[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:14]=1[CH2:15][N:16]1[CH2:21][CH2:20][CH:19](/[CH:22]=[C:9]2/[C:5]([NH:4][CH2:3][CH2:2][OH:1])=[N:6][C:7](=[O:10])[S:8]/2)[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 3014295Piperidinium acetateHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178518158HCID 178518158, compound

Product 1

HCID 178518153HCID 178518153, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-[(2-hydroxyethyl)amino]-1,3-thiazol-2(5H)-one (1.20 g) and 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (2.54 g) in 2-propanol (20 mL) was added piperidinium acetate (1.09 g) 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, methanol/ethyl acetate) and recrystallized from ethyl acetate/heptane to give the title compound (1.12 g)

Workup

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

Sources & evidence

ORD record
ord-2ccb463395894070b3ff675d2b038d67
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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