Piperidinium acetate → HCID 178464089, compound

HRID 1620534Notes

Reaction equation

HRID 1620534 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.[CH2:24]([N:26]([CH2:39][CH3:40])[CH2:27][CH2:28][O:29][CH2:30][CH2:31][NH:32][C:33]1[CH2:37][S:36][C:35](=[O:38])[N:34]=1)[CH3:25].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:37]2/[C:33]([NH:32][CH2:31][CH2:30][O:29][CH2:28][CH2:27][N:26]([CH2:24][CH3:25])[CH2:39][CH3:40])=[N:34][C:35](=[O:38])[S:36]/2)[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 3014295Piperidinium acetateHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178464088HCID 178464088, compound

Product 1

HCID 178464089HCID 178464089, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (1.21 g) in 2-propanol (15 mL) was added a solution of 4-({2-[2-(diethylamino)ethoxy]ethyl}amino)-1,3-thiazol-2(5H)-one (1.85 g) in 2-propanol (5 mL), and piperidinium acetate (0.52 g) was added. The reaction mixture was stirred at 60° C. overnight and concentrated. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate) to give the title compound (1.26 g).

Workup

  1. additionwas added
  2. concentrationconcentrated
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate)

Sources & evidence

ORD record
ord-a2238f892b0640ef975c8d8b476d9985
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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