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

HRID 2208669Notes

Reaction equation

[CH2:1]([N:3]([CH:19]1[CH2:24][CH2:23][N:22]([CH:25]([CH3:27])[CH3:26])[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]([CH:25]([CH3:26])[CH3:27])[CH2:21][CH2:20]1)[C:4]1[C:5]([CH3:18])=[C:6]([CH:11]=[C:12]([C:14]([F:15])([F:17])[F:16])[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-(propan-2-yl)piperidin-4-yl]amino}-2-methyl-5-(trifluoromethyl)benzoate (220 mg, 0.569 mmol) in methanol (4 mL) was added aq. NaOH (5M, 170 ul, 0.854 mmol). The reaction mixture was stirred at 50° C. for 2 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 (510 mg).

Workup

temperatureAfter cooling to 23° C
concentrationwas concentrated in vacuo

Sources & evidence

ORD record: ord-65d02d3819844317805eec6fb8aea163
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376422B2

Reaction notes

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