Piperidinium acetate → HCID 178448316, compound

HRID 1620759Notes

Reaction equation

HRID 1620759 reaction equation
[CH3:1][N:2]([CH3:16])[C:3](=[O:15])[C@@H:4]([CH:12]([CH3:14])[CH3:13])[NH:5][C:6]1[CH2:10][S:9][C:8](=[O:11])[N:7]=1.[F:17][C:18]([F:39])([F:38])[C:19]1[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][C:20]=1[CH2:21][N:22]1[CH2:27][CH2:26][CH:25]([CH:28]=O)[CH2:24][CH2:23]1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:39][C:18]([F:17])([F:38])[C:19]1[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][C:20]=1[CH2:21][N:22]1[CH2:27][CH2:26][CH:25](/[CH:28]=[C:10]2/[C:6]([NH:5][C@@H:4]([C:3]([N:2]([CH3:1])[CH3:16])=[O:15])[CH:12]([CH3:14])[CH3:13])=[N:7][C:8](=[O:11])[S:9]/2)[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 3014295Piperidinium acetateHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178448319HCID 178448319, compound

Product 1

HCID 178448316HCID 178448316, compoundYield 62%

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-valinamide (0.730 g) and 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (1.018 g) in 2-propanol (10 mL) was added piperidinium acetate (0.436 g) under ice-cooling. 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 (1.050 g).

Workup

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

Sources & evidence

ORD record
ord-e846200d836a441aa354ca383db5a009
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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