Sodium Hydroxide → 4-(4-Methylpiperazin-1-yl)-3-(trifluoromethyl)benzoic acid

HRID 1441739Notes

Reaction equation

[O:1]1[CH2:6][CH2:5]OCC1.[OH-:7].[Na+].[CH3:9][N:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:23]=[CH:22]C(C#N)=[CH:18][C:17]=2[C:24]([F:27])([F:26])[F:25])[CH2:12][CH2:11]1>O>[CH3:9][N:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:23]=[CH:22][C:5]([C:6]([OH:1])=[O:7])=[CH:18][C:17]=2[C:24]([F:27])([F:26])[F:25])[CH2:12][CH2:11]1

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture consisting of 30 mL dioxane, 15 mL water and 11.25 mL of 2M aqueous sodium hydroxide solution is added to 4-(4-methyl-1-piperazinyl)-3-(trifluoromethyl)-benzonitrile and the reaction mixture is shaken for 16 hours at 95° C. After cooling, the mixture is evaporated. The resulting residue is treated with water, the pH adjusted to ˜5-6 with 1M hydrochloric acid and the solvent evaporated off under reduced pressure. The residue is treated with hot methanol, the insoluble salt filtered off and the filtrate evaporated yielding the crude title compound which is used for the next step without further purification.

Workup

temperatureAfter cooling
customthe mixture is evaporated
additionThe resulting residue is treated with water
customthe solvent evaporated off under reduced pressure
additionThe residue is treated with hot methanol
filtrationthe insoluble salt filtered off
customthe filtrate evaporated

Sources & evidence

ORD record: ord-096df4ca2f2c422b90cd6516be36cd23
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07655669B2

Reaction notes

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