Piperidinium acetate → HCID 178518140, compound

HRID 1620720Notes

Reaction equation

HRID 1620720 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH2:10][S:9][C:8](=[O:11])[N:7]=1.[F:12][C:13]([F:34])([F:33])[C:14]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:15]=1[CH2:16][N:17]1[CH2:22][CH2:21][CH:20]([CH:23]=O)[CH2:19][CH2:18]1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:34][C:13]([F:12])([F:33])[C:14]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:15]=1[CH2:16][N:17]1[CH2:22][CH2:21][CH:20](/[CH:23]=[C:10]2/[C:6]([NH:5][CH2:4][CH2:3][CH2:2][OH:1])=[N:7][C:8](=[O:11])[S:9]/2)[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 3014295Piperidinium acetateHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178518141HCID 178518141, compound

Product 1

HCID 178518140HCID 178518140, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-[(3-hydroxypropyl)amino]-1,3-thiazol-2(5H)-one (900 mg) and 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (1.75 g) in 2-propanol (20 mL) was added piperidinium acetate (750 mg) at room temperature. The reaction mixture was stirred at 60° C. overnight. After evaporation of the solvent, the residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate) and recrystallized from ethyl acetate/heptane to give the title compound (1.17 g).

Workup

  1. customAfter evaporation of the solvent
  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-0cb41096c8c5404b9679a025fadbd1a5
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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