1-Hydroxybenzotriazole → N-[2-oxo-3-(2-trifluoromethylphenyl)piperidin-1-yl]-3-p-tolylsulfanylpropionamide

HRID 546776Notes

Reaction equation

HRID 546776 reaction equation
C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.[NH2:20][N:21]1[CH2:26][CH2:25][CH2:24][CH:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]([F:36])([F:35])[F:34])[C:22]1=[O:37].[CH3:38][C:39]1[CH:44]=[CH:43][C:42]([S:45][CH2:46][CH2:47][C:48](O)=[O:49])=[CH:41][CH:40]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C.C(Cl)CCl>[O:37]=[C:22]1[CH:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]([F:34])([F:35])[F:36])[CH2:24][CH2:25][CH2:26][N:21]1[NH:20][C:48](=[O:49])[CH2:47][CH2:46][S:45][C:42]1[CH:43]=[CH:44][C:39]([CH3:38])=[CH:40][CH:41]=1

Participants

9

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 836943-((4-Methylphenyl)thio)propionic acidHCID 516892Sodium BicarbonateHCID 666173261-Amino-3-(2-trifluoromethylphenyl)piperidin-2-one

Product 1

HCID 66839674N-[2-oxo-3-(2-trifluoromethylphenyl)piperidin-1-yl]-3-p-tolylsulfanylpropionamideYield 98.9%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

EDC (9.01 g), HOBT (6.34 g) and IPEA (21.8 ml) were added to a solution of 1-amino-3-(2-trifluoromethylphenyl)piperidin-2-one (8.08 g) and 3-[(4-methylphenyl)thio]propionic acid (7.37 g) in DMF (80 ml) under cooling in an ice water bath. The reaction solution was stirred at room temperature for four hours. Ethyl acetate and a sodium bicarbonate solution were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and then the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (13.51 g). The property values of the compound are as follows.

Workup

  1. temperatureunder cooling in an ice water bath
  2. customthe organic layer was separated
  3. washThe resulting organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe drying agent was separated by filtration
  6. concentrationthe organic layer was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8bcbff4a51fb4bc79e19acf0d3a6085b
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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