Hydrochloric Acid → 6-(1-Isopropyl-piperidin-4-yloxy)-benzo[b]thiophene-2-carboxylic acid

HRID 493185Notes

Reaction equation

HRID 493185 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[C:12]([O:15][CH:16]3[CH2:21][CH2:20][N:19]([CH:22]([CH3:24])[CH3:23])[CH2:18][CH2:17]3)[CH:13]=[CH:14][C:8]=2[CH:7]=1)=[O:5])C.[OH-].[Na+].Cl>C1COCC1.C(O)C>[CH:22]([N:19]1[CH2:20][CH2:21][CH:16]([O:15][C:12]2[CH:13]=[CH:14][C:8]3[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[S:10][C:9]=3[CH:11]=2)[CH2:17][CH2:18]1)([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 687272376-(1-Isopropyl-piperidin-4-yloxy)-benzo[b]thiophene-2-carboxylic acid ethyl ester

Product 1

HCID 687277496-(1-Isopropyl-piperidin-4-yloxy)-benzo[b]thiophene-2-carboxylic acidYield 144%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

The above prepared 6-(1-isopropyl-piperidin-4-yloxy)-benzo[b]thiophene-2-carboxylic acid ethyl ester (0.359 g, 1.033 mmol) was dissolved in 2 mL of THF/ethanol=1/1 and treated with 0.517 mL of aq. NaOH (3M, 1.5 eq.). The mixture was stirred for 1 h at ambient temperature and was then neutralized by adding 0.77 mL of 2M HCl (1.5 eq.). Careful evaporation of all solvents and drying afforded then 0.475 g of the title compound as white solid contaminated with innocouos inorganic salts.

Workup

  1. customCareful evaporation of all solvents
  2. customdrying
  3. customafforded

Sources & evidence

ORD record
ord-ca80c4feea694a61b3f55b2b05971f13
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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