1-Methylpiperazine → 3-[4-(4-Chlorophenyl)-2-(4-methyl-1-piperazinyl)-5-oxazolyl]propionic acid

HRID 350728Notes

Reaction equation

HRID 350728 reaction equation
Cl[C:2]1[O:3][C:4]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:6]=1.[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>C(O)(C)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:6]=[C:2]([N:23]3[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]3)[O:3][C:4]=2[CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 118082582-Chloro-4-(4-chlorophenyl)-5-oxazolepropionic acid

Product 1

HCID 210886393-[4-(4-Chlorophenyl)-2-(4-methyl-1-piperazinyl)-5-oxazolyl]propionic acidYield 78.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixed solution of 3-[2-chloro-4-(4-chlorophenyl)-5-oxazolyl]propionic acid (1.43 g), 1-methylpiperazine (2.5 g) and isopropyl alcohol (20 mL) was heated under reflux for 10 hrs. The reaction mixture was concentrated, diluted with water, and acidified with 2N aqueous hydrochloric acid solution. The precipitated crystals were collected by filtration and recrystallized from ethanol to give 3-[4-(4-chlorophenyl)-2-(4-methyl-1-piperazinyl)-5-oxazolyl]propionic acid (1.37 g, yield 70%) as colorless prism crystals. melting point: 157–160° C.

Workup

  1. temperatureunder reflux for 10 hrs
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with water
  4. filtrationThe precipitated crystals were collected by filtration
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-2b259809568d4908875b16275f2ff930
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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