Piperidinium acetate → HCID 86678888, compound

HRID 1620726Notes

Reaction equation

HRID 1620726 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]([C@@H:5]1[CH2:8][CH2:7][N:6]1[C:9]1[CH2:13][S:12][C:11](=[O:14])[N:10]=1)=[O:4].[F:16][C:17]([F:38])([F:37])[C:18]1[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:19]=1[CH2:20][N:21]1[CH2:26][CH2:25][CH:24]([CH:27]=O)[CH2:23][CH2:22]1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:38][C:17]([F:16])([F:37])[C:18]1[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:19]=1[CH2:20][N:21]1[CH2:26][CH2:25][CH:24](/[CH:27]=[C:13]2/[C:9]([N:6]3[CH2:7][CH2:8][C@H:5]3[C:3]([N:2]([CH3:15])[CH3:1])=[O:4])=[N:10][C:11](=[O:14])[S:12]/2)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 3014295Piperidinium acetateHCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 86678889HCID 86678889, compound

Product 1

HCID 86678888HCID 86678888, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (2S)—N,N-dimethyl-1-(2-oxo-2,5-dihydro-1,3-thiazol-4-yl)azetidine-2-carboxamide (682 mg) and 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (1018 mg) is in 2-propanol (10 mL) was added piperidinium acetate (436 mg) at room temperature. The reaction mixture was stirred at 60° C. overnight, and the solvent was evaporated. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) and recrystallized from ethyl acetate/heptane to give the title compound (590 mg).

Workup

  1. customthe solvent was evaporated
  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-497d76928dbb4a1e974037e668f6b914
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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