Hydrochloric Acid → 5-Chloro-3-[ethyl(1-methylpiperidin-4-yl)amino]-2-methylbenzoic acid

HRID 2208676Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of methyl 5-chloro-3-[ethyl(1-methylpiperidin-4-yl)amino]-2-methylbenzoate (1.06 g, 3.26 mmol) in methanol (10 mL) was added aq. NaOH (5 M, 780 ul, 3.92 mmol). The reaction mixture was stirred at 50° C. for 18 hours. After cooling to 23° C., HCl (2 M, 2 mL)) was added to the mixture and the mixture was acidified to pH=5 and was concentrated in vacuo to give the titled compound as crude products (1.80 g).

Workup

temperatureAfter cooling to 23° C.
concentrationwas concentrated in vacuo

Sources & evidence

ORD record: ord-37487ddac5294e7ab62cd39a45bc5754
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376422B2

Reaction notes

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