Piperidinium acetate → HCID 178462000, compound

HRID 1620718Notes

Reaction equation

HRID 1620718 reaction equation
[CH3:1][N:2]([CH3:14])[C:3](=[O:13])[C@@H:4]([CH3:12])[NH:5][C:6]1[CH2:10][S:9][C:8](=[O:11])[N:7]=1.[F:15][C:16]([F:37])([F:36])[C:17]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:18]=1[CH2:19][N:20]1[CH2:25][CH2:24][CH:23]([CH:26]=O)[CH2:22][CH2:21]1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:37][C:16]([F:15])([F:36])[C:17]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:18]=1[CH2:19][N:20]1[CH2:25][CH2:24][CH:23](/[CH:26]=[C:10]2/[C:6]([NH:5][C@@H:4]([C:3]([N:2]([CH3:1])[CH3:14])=[O:13])[CH3:12])=[N:7][C:8](=[O:11])[S:9]/2)[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 3014295Piperidinium acetateHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178462002HCID 178462002, compound

Product 1

HCID 178462000HCID 178462000, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N,N-dimethyl-N2-(2-oxo-2,5-dihydro-1,3-thiazol-4-yl)-D-alaninamide (1.02 g) and 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (1.93 g) in 2-propanol (10 mL) was added piperidinium acetate (826 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 (1.30 g)

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-1a26126be33a45d38ddd34ad3dd9e5e2
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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