Hydrochloric Acid → 2-(2-Hydroxy-5-(1-methylpiperidin-4-yl)benzamido)-4-phenylbenzoic acid

HRID 454576Notes

Reaction equation

[OH-].[Na+].[OH:3][C:4]1[CH:28]=[CH:27][C:26]([CH:29]2[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]2)=[CH:25][C:5]=1[C:6]([NH:8][C:9]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=[CH:15][C:10]=1[C:11]([O:13]C)=[O:12])=[O:7].Cl>CO>[OH:3][C:4]1[CH:28]=[CH:27][C:26]([CH:29]2[CH2:30][CH2:31][N:32]([CH3:35])[CH2:33][CH2:34]2)=[CH:25][C:5]=1[C:6]([NH:8][C:9]1[CH:18]=[C:17]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:16]=[CH:15][C:10]=1[C:11]([OH:13])=[O:12])=[O:7]

Participants

Conditions

Temperature: 60 °C

Procedure

A 2.0 mol/L aqueous solution of sodium hydroxide (0.33 mL) was added to a methanol (2.0 mL) suspension of the obtained methyl 2-(2-hydroxy-5-(1-methylpiperidin-4-yl)benzamido)-4-phenylbenzoate (0.058 g), followed by stirring at 60° C. for 9 hours and 20 minutes. The reaction mixture was cooled to room temperature, and 6 mol/L hydrochloric acid (0.11 mL) was added thereto. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 95-85% chloroform/methanol] to obtain 0.019 g of 2-(2-hydroxy-5-(1-methylpiperidin-4-yl)benzamido)-4-phenylbenzoic acid as a white solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
customThe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography [eluent: 95-85% chloroform/methanol]

Sources & evidence

ORD record: ord-d817427eb2b5422ca232ca8dacbf2642
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492582B2

Reaction notes

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