Sodium Hydroxide → 1-[4-(5-Trifluoromethylpyridin-2-yl)-piperazin-1-yl]-cyclopropanecarboxylic acid

HRID 386523Notes

Reaction equation

HRID 386523 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3([C:18]([O:20]C)=[O:19])[CH2:17][CH2:16]3)[CH2:11][CH2:10]2)=[N:7][CH:8]=1.[OH-].[Na+]>O1CCCC1.CO>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3([C:18]([OH:20])=[O:19])[CH2:17][CH2:16]3)[CH2:11][CH2:10]2)=[N:7][CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66628341Methyl 1-[4-(5-trifluoromethylpyridin-2-yl)-piperazin-1-yl]-cyclopropanecarboxylate

Product 1

HCID 666284741-[4-(5-Trifluoromethylpyridin-2-yl)-piperazin-1-yl]-cyclopropanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of methyl 1-[4-(5-trifluoromethylpyridin-2-yl)-piperazin-1-yl]-cyclopropanecarboxylate (0.32 g, 0.96 mmol) from Example 16D in tetrahydrofuran (5 mL) and methanol (2 mL) was treated with 4 N sodium hydroxide (2.40 mL, 9.60 mmol) and stirred overnight at 60° C. Reaction mixture concentrated under reduced pressure and dissolved in water. Solution neutralized with 1 N phosphoric acid (pH 7) and extracted three times with chloroform. Extracts dried over Na2SO4, filtered, and concentrated under reduced pressure to afford the title compound without further purification. MS (ESI) m/z 316 (M+H)+.

Workup

  1. customReaction mixture
  2. concentrationconcentrated under reduced pressure
  3. dissolutiondissolved in water
  4. extractionextracted three times with chloroform
  5. dry with materialExtracts dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9f40654260ab481cb8f30ee65c9a732c
Source dataset
uspto-grants-2013_02
Patent number
US08372841B2

Reaction notes

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