Potassium Carbonate → n-{3-[4-(5-Chloro-2-hydroxyphenyl)-1-piperazinyl]propyl}-5-methyl-3-phenylisoxazole-4-carboxamide

HRID 1840285Notes

Reaction equation

HRID 1840285 reaction equation
Cl[CH2:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:10][O:11][C:12]=1[CH3:13])=[O:7].Br.Br.[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([OH:35])=[C:27]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([OH:35])=[C:27]([N:29]2[CH2:30][CH2:31][N:32]([CH2:2][CH2:3][CH2:4][NH:5][C:6]([C:8]3[C:9]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)=[N:10][O:11][C:12]=3[CH3:13])=[O:7])[CH2:33][CH2:34]2)[CH:28]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23447862HCID 23447862, compoundHCID 234479081-(5-Chloro-2-hydroxyphenyl)piperazine dihydrobromide

Product 1

HCID 9846794n-{3-[4-(5-Chloro-2-hydroxyphenyl)-1-piperazinyl]propyl}-5-methyl-3-phenylisoxazole-4-carboxamideYield 125.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 0.28 g of Compound 2B, 0.21 g of Compound 2A and 0.14 g of potassium carbonate was heated at 160° C. for 20 minutes. After cooling to room temperature, the mixture was taken up with 8 mL of chloroform, and inorganic matter was filtered off. The filtrate was evaporated to dryness and purified by flash chromatography (chloroform:methanol 97.5:2.5) to yield 0.32 g (71%) of the title compound. M.p. 92-98° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationwas filtered off
  3. customThe filtrate was evaporated to dryness
  4. custompurified by flash chromatography (chloroform:methanol 97.5:2.5)

Sources & evidence

ORD record
ord-784aa77ec3484683b8cec329a0b93cf2
Source dataset
uspto-grants-2004_01
Patent number
US06680319B2

Reaction notes

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