Sodium Hydroxide → trans-2-[4-(6-Trifluoromethyl-benzo[b]thiophen-3-yl)-piperazin-1-ylmethyl]-cyclopropanecarboxylic acid

HRID 501278Notes

Reaction equation

HRID 501278 reaction equation
[OH-].[Na+].C[O:4][C:5]([C@@H:7]1[CH2:9][C@H:8]1[CH2:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:18]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:19]=3[S:20][CH:21]=2)[CH2:13][CH2:12]1)=[O:6]>O1CCOCC1.CO>[F:28][C:26]([F:27])([F:29])[C:23]1[CH:24]=[CH:25][C:18]2[C:17]([N:14]3[CH2:15][CH2:16][N:11]([CH2:10][C@@H:8]4[CH2:9][C@H:7]4[C:5]([OH:6])=[O:4])[CH2:12][CH2:13]3)=[CH:21][S:20][C:19]=2[CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68456225trans-2-[4-(6-Trifluoromethyl-benzo[b]thiophen-3-yl)-piperazin-1-ylmethyl]-cyclopropanecarboxylic Acid Methyl Ester

Product 1

HCID 18436982trans-2-[4-(6-Trifluoromethyl-benzo[b]thiophen-3-yl)-piperazin-1-ylmethyl]-cyclopropanecarboxylic acidYield 81%

Reagents, catalysts & solvents 1

HCID 21966525Dioxane MethanolSolvent

Procedure

Add 5N NaOH solution (425 mL, 226 mmol) to a solution of trans-2-[4-(6-trifluoromethyl-benzo[b]thiophen-3-yl)-piperazin-1-ylmethyl]-cyclopropanecarboxylic acid methyl ester, Example 6a, (18.0 g, 45.1 mmol) in dioxane/methanol (400 mL, 3:1) and heat the reaction at 60° C. for 6 h. Selectively remove most of the methanol and acidify the remaining dioxane solution to pH 5-6 with 2N acetic acid. Collect the desired compound, which precipitates from solution, to obtain 14.08 g (81%) of colorless crystals, m/z=385 (M+H)+

Workup

  1. temperatureheat
  2. customthe reaction at 60° C. for 6 h
  3. customSelectively remove most of the methanol
  4. customCollect the desired compound, which
  5. customprecipitates from solution

Sources & evidence

ORD record
ord-20c3404a6def4f55a4c6877a9a9218b5
Source dataset
uspto-grants-2010_08
Patent number
US07772252B2

Reaction notes

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