Piperidinium acetate → HCID 178445936, compound

HRID 1620704Notes

Reaction equation

HRID 1620704 reaction equation
[CH3:1][N:2]([CH3:17])[C:3](=[O:16])[C@H:4]([CH2:12][CH:13]([CH3:15])[CH3:14])[NH:5][C:6]1[CH2:10][S:9][C:8](=[O:11])[N:7]=1.[F:18][C:19]([F:40])([F:39])[C:20]1[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[CH:31][C:21]=1[CH2:22][N:23]1[CH2:28][CH2:27][CH:26]([CH:29]=O)[CH2:25][CH2:24]1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:40][C:19]([F:18])([F:39])[C:20]1[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[CH:31][C:21]=1[CH2:22][N:23]1[CH2:28][CH2:27][CH:26](/[CH:29]=[C:10]2/[C:6]([NH:5][C@H:4]([C:3]([N:2]([CH3:1])[CH3:17])=[O:16])[CH2:12][CH:13]([CH3:14])[CH3:15])=[N:7][C:8](=[O:11])[S:9]/2)[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 3014295Piperidinium acetateHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178445937HCID 178445937, compound

Product 1

HCID 178445936HCID 178445936, compoundYield 51.2%

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)-L-leucinamide (772 mg) and 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (1221 mg) in 2-propanol (10 mL) was added piperidinium acetate (523 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, ethyl acetate/hexane) and recrystallized from ethyl acetate/heptane to give the title compound (888 mg).

Workup

  1. customAfter evaporation of the solvent
  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-4be0f34691524747b4573d8241edbe5d
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

Loading…