Potassium Sodium Tartrate → 3-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid piperidin-1-yl-amide

HRID 1920902Notes

Reaction equation

HRID 1920902 reaction equation
C[Al](C)C.[NH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C[O:13][C:14]([C:16]1[O:20][N:19]=[C:18]([O:21][CH2:22][C:23]2[C:24]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:25][O:26][C:27]=2[CH3:28])[CH:17]=1)=O.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>O1CCOCC1>[N:6]1([NH:5][C:14]([C:16]2[O:20][N:19]=[C:18]([O:21][CH2:22][C:23]3[C:24]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[N:25][O:26][C:27]=3[CH3:28])[CH:17]=2)=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 9357Potassium Sodium TartrateHCID 166581-AminopiperidineHCID 16682925TrimethylaluminumHCID 674922963-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester

Product 1

HCID 468969833-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid piperidin-1-yl-amideYield 82%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of trimethylaluminium (2 M in toluene, 0.6 mL, 1.3 mmol) was added dropwise (exothermic) to a solution of 1-aminopiperidine (127 mg, 1.3 mmol) in dioxane (3 mL) and the resulting mixture was stirred at room temperature for 1 h. Then a solution of 3-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-isoxazole-5-carboxylic acid methyl ester (100 mg, 0.32 mmol) in dioxane (2 mL) was added. The resulting mixture was then heated at 85-90° C. for 4 h and then cooled to room temperature, stirred overnight, and then poured into Seignette's salt and extracted with ethyl acetate which was then washed with brine, dried over sodium sulfate and evaporated. Purification by chromatography (silica, dichloromethane:methanol=9:1 to 4:1) afforded the title compound (100 mg, 82%) which was obtained as a white solid. MS: m/e=383.3 [M+H]+.

Workup

  1. temperatureThe resulting mixture was then heated at 85-90° C. for 4 h
  2. temperaturecooled to room temperature
  3. stirringstirred overnight
  4. extractionextracted with ethyl acetate which
  5. washwas then washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customPurification by chromatography (silica, dichloromethane:methanol=9:1 to 4:1)

Sources & evidence

ORD record
ord-6191dcc4783047bdbb5ec8b188951063
Source dataset
uspto-grants-2012_05
Patent number
US08173652B2

Reaction notes

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