Hydrochloric Acid → 6-(Piperidin-4-yloxy)-benzo[b]thiophene-2-carboxylic acid ethyl ester

HRID 493198Notes

Reaction equation

HRID 493198 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]3[CH:22]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[S:20][C:19]=3[CH:28]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[CH2:26]([O:25][C:23]([C:21]1[S:20][C:19]2[CH:28]=[C:15]([O:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[CH:16]=[CH:17][C:18]=2[CH:22]=1)=[O:24])[CH3:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 687265814-(2-Ethoxycarbonyl-benzo[b]thiophen-6-yloxy)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 688803516-(Piperidin-4-yloxy)-benzo[b]thiophene-2-carboxylic acid ethyl esterYield 105%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The above prepared 4-(2-ethoxycarbonyl-benzo[b]thiophen-6-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (0.330 g, 0.814 mmol) was dissolved in 2 mL of dioxane and treated with HCl (4.1 mL of 4N [dioxane], 20 eq.) and the mixture kept at ambient temperature for 2 h. Reducing the volume, adding heptane, and direct crystallization produced 0.261 g of 6-(piperidin-4-yloxy)-benzo[b]thiophene-2-carboxylic acid ethyl ester as hydrochloride as white crystals, which was further processed as follows:

Workup

  1. additionadding
  2. customheptane, and direct crystallization

Sources & evidence

ORD record
ord-a28af906e85e40d78a296d4b5fadd2eb
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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