Hydrochloric Acid → 2-methoxy-5-{4-[1-(2-methoxyethyl)-1H-indol-3-yl]piperidin-1-ylmethyl}benzoic acid

HRID 227274Notes

Reaction equation

HRID 227274 reaction equation
C([O:3][C:4](=[O:33])[C:5]1[CH:10]=[C:9]([CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]([CH2:27][CH2:28][O:29][CH3:30])[CH:19]=3)[CH2:14][CH2:13]2)[CH:8]=[CH:7][C:6]=1[O:31][CH3:32])C.[OH-].[Na+].Cl>CO.O1CCCC1>[CH3:32][O:31][C:6]1[CH:7]=[CH:8][C:9]([CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]([CH2:27][CH2:28][O:29][CH3:30])[CH:19]=3)[CH2:14][CH2:13]2)=[CH:10][C:5]=1[C:4]([OH:33])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 689704652-methoxy-5-{4-[1-(2-methoxyethyl)-1H-indol-3-yl]piperidin-1-ylmethy}-benzoic acid ethyl ester

Product 1

HCID 99796512-methoxy-5-{4-[1-(2-methoxyethyl)-1H-indol-3-yl]piperidin-1-ylmethyl}benzoic acidYield 65.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Over a solution of 0.9 g (0.002 mol) of 2-methoxy-5-{4-[1-(2-methoxyethyl)-1H-indol-3-yl]piperidin-1-ylmethy}-benzoic acid ethyl ester in 9 ml of methanol and 5 ml of tetrahydrofuran, 5 ml of a 1N aqueous sodium hydroxide were added. The crude mixture was stirred at room temperature for 20 hours and then neutralised with 1 N aqueous HCl. The product precipitated from the mixture. The solid obtained was filtrated and washed with ethanol and ethyl ether. 0.55 g (65% of yield) of 2-methoxy-5-{4-[1-(2-methoxyethyl)-1H-indol-3-yl]piperidin-1-ylmethyl}-benzoic acid were obtained.

Workup

  1. customThe product precipitated from the mixture
  2. customThe solid obtained
  3. filtrationwas filtrated
  4. washwashed with ethanol and ethyl ether

Sources & evidence

ORD record
ord-223506bf78e54f3da925cbb435651b04
Source dataset
uspto-grants-2009_07
Patent number
US07560471B2

Reaction notes

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