Hydrochloric Acid → 5-Chloro-6-(1-isopropyl-piperidin-4-yloxy)-3-methyl-benzofuran-2-carboxylic acid

HRID 493222Notes

Reaction equation

HRID 493222 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[C:14]([O:16][CH:17]3[CH2:22][CH2:21][N:20]([CH:23]([CH3:25])[CH3:24])[CH2:19][CH2:18]3)[C:13]([Cl:26])=[CH:12][C:9]=2[C:10]=1[CH3:11])=[O:5])C.[OH-].[Na+].Cl>C1COCC1.C(O)C>[Cl:26][C:13]1[C:14]([O:16][CH:17]2[CH2:22][CH2:21][N:20]([CH:23]([CH3:25])[CH3:24])[CH2:19][CH2:18]2)=[CH:15][C:8]2[O:7][C:6]([C:4]([OH:5])=[O:3])=[C:10]([CH3:11])[C:9]=2[CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 687236245-Chloro-6-(1-isopropyl-piperidin-4-yloxy)-3-methyl-benzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 687236205-Chloro-6-(1-isopropyl-piperidin-4-yloxy)-3-methyl-benzofuran-2-carboxylic acidYield 139.8%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

The above prepared 5-chloro-6-(1-isopropyl-piperidin-4-yloxy)-3-methyl-benzofuran-2-carboxylic acid ethyl ester (0.897 g, 2.36 mmol) was dissolved in 4.8 mL of THF/ethanol=1/1 and treated with 1.18 mL of aq. NaOH (3M, 1.5 eq.). The mixture was stirred for 3 h at ambient temperature and was then neutralized by adding 1.77 mL of 2M HCl (1.5 eq.). Careful evaporation of all solvents and drying afforded finally 1.161 g of the title compound as off-white solid, contaminated with innocuous inorganic salts.

Workup

  1. customCareful evaporation of all solvents
  2. customdrying

Sources & evidence

ORD record
ord-88b177e259084b6a8995629b5a6d35d8
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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