Piperidinium acetate → HCID 178518113, compound

HRID 1620747Notes

Reaction equation

HRID 1620747 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][NH:7][C:8]1[CH2:12][S:11][C:10](=[O:13])[N:9]=1.[F:14][C:15]([F:36])([F:35])[C:16]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:17]=1[CH2:18][N:19]1[CH2:24][CH2:23][CH:22]([CH:25]=O)[CH2:21][CH2:20]1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:36][C:15]([F:14])([F:35])[C:16]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:17]=1[CH2:18][N:19]1[CH2:24][CH2:23][CH:22](/[CH:25]=[C:12]2/[C:8]([NH:7][CH2:6][C:2]3[O:1][CH:5]=[CH:4][N:3]=3)=[N:9][C:10](=[O:13])[S:11]/2)[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 3014295Piperidinium acetateHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178518114HCID 178518114, compound

Product 1

HCID 178518113HCID 178518113, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-[(1,3-oxazol-2-ylmethyl)amino]-1,3-thiazol-2(5H)-one (357 mg) and 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (676 mg) in 2-propanol (5 mL) was added piperidinium acetate (289 mg) at room temperature. The reaction mixture was stirred at 60° C. for 5 hr, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate) and recrystallized from ethyl acetate/heptane to give the title compound (751 mg)

Workup

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

Sources & evidence

ORD record
ord-6f5835786c4245178670f920b0a4ddd2
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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