Hydrochloric Acid → 5-(1-Isopropyl-piperidin-4-yloxy)-benzo[b]thiophene-2-carboxylic acid

HRID 493180Notes

Reaction equation

HRID 493180 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][C:12]([O:14][CH:15]3[CH2:20][CH2:19][N:18]([CH:21]([CH3:23])[CH3:22])[CH2:17][CH2:16]3)=[CH:13][C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+].Cl>C1COCC1.C(O)C>[CH:21]([N:18]1[CH2:19][CH2:20][CH:15]([O:14][C:12]2[CH:11]=[CH:10][C:8]3[S:9][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=3[CH:13]=2)[CH2:16][CH2:17]1)([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 687252665-(1-Isopropyl-piperidin-4-yloxy)-benzo[b]thiophene-2-carboxylic acid methyl ester

Product 1

HCID 687282875-(1-Isopropyl-piperidin-4-yloxy)-benzo[b]thiophene-2-carboxylic acidYield 120.3%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

The above prepared 5-(1-isopropyl-piperidin-4-yloxy)-benzo[b]thiophene-2-carboxylic acid methyl ester (0.222 g, 0.666 mmol) was dissolved in 1.3 mL of THF/ethanol=1/1 and treated with 0.333 mL of aq. NaOH (3M, 1.5 eq.). The mixture was stirred for 2 h at ambient temperature and was then neutralized by adding 0.50 mL of 2M HCl (1.5 eq.). Careful evaporation of all solvents, trituration in diethyl ether, and drying afforded then 0.256 g of the title compound as white solid, contaminated with innocouos inorganic salts.

Workup

  1. customCareful evaporation of all solvents, trituration in diethyl ether
  2. customdrying
  3. customafforded

Sources & evidence

ORD record
ord-0b7521c40a0d4f8fa477918d17424b3d
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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