Hydrochloric Acid → 3-[Ethyl(1-methylpiperidin-4-yl)amino]-2-methyl-5-(trifluoromethyl)benzoic acid

HRID 2208668Notes

Reaction equation

[CH2:1]([N:3]([CH:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1)[C:4]1[C:5]([CH3:18])=[C:6]([CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1)[C:7]([O:9]C)=[O:8])[CH3:2].[OH-].[Na+].Cl>CO>[CH2:1]([N:3]([CH:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1)[C:4]1[C:5]([CH3:18])=[C:6]([CH:11]=[C:12]([C:14]([F:16])([F:15])[F:17])[CH:13]=1)[C:7]([OH:9])=[O:8])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of methyl 3-[ethyl(1-methylpiperidin-4-yl)amino]-2-methyl-5-(trifluoromethyl)benzoate (700 mg, 1.95 mmol) in methanol (15 mL) was added aq. NaOH (5M, 590 ul, 2.93 mmol). The reaction mixture was stirred at 50° C. for 3 hours. After cooling to 23° C., HCl (2 M) was added to the mixture. The mixture was acidified to pH=5 and was concentrated in vacuo to give the titled compound as crude products (1.26 g).

Workup

temperatureAfter cooling to 23° C.
concentrationwas concentrated in vacuo

Sources & evidence

ORD record: ord-d956bc9de5864c448b1b89525fdc5b48
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376422B2

Reaction notes

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