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

HRID 1504201Notes

Reaction equation

HRID 1504201 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. Methanol 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-701b4f0a24ec4af4a0214e028d47502f
Source dataset
uspto-grants-2015_12
Patent number
US09212187B2

Reaction notes

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