Hydrochloric Acid → 2-{3-[N-(2-pyridin-3-ylethyl)-N-(pyridin-4-ylmethyl)amino]propoxy}benzoic acid

HRID 69030Notes

Reaction equation

HRID 69030 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:33])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)[CH2:18][C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)C.Cl>CO>[N:29]1[CH:30]=[CH:31][CH:32]=[C:27]([CH2:26][CH2:25][N:17]([CH2:16][CH2:15][CH2:14][O:13][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([OH:33])=[O:5])[CH2:18][C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[CH:28]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 669600122-{3-[N-(2-pyridin-3-ylethyl)-N-(pyridin-4-ylmethyl)amino]propoxy}benzoic acid ethyl ester

Product 1

HCID 867626992-{3-[N-(2-pyridin-3-ylethyl)-N-(pyridin-4-ylmethyl)amino]propoxy}benzoic acidYield 131.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 1N-sodium hydroxide aqueous solution (1.8 ml) was added to a methanol solution (3 ml) of 2-{3-[N-(2-pyridin-3-ylethyl)-N-(pyridin-4-ylmethyl)amino]propoxy}benzoic acid ethyl ester (372 mg). The mixture was stirred at room temperature overnight. 6N-Hydrochloric acid (0.3 ml) was added to the reaction mixture and condensed under reduced pressure. Metanol was added to the residue, and the generated insoluble matter was separated by filtration. The filtrate was condensed under reduced pressure to give the title compound (458 mg) as a colorless oil.

Workup

  1. customthe generated insoluble matter was separated by filtration
  2. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-2f0ff8923a5f4daea9a15a3398d714be
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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