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

HRID 1361433Notes

Reaction equation

HRID 1361433 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-8b1d9bd74bc943acabb186cc7856158b
Source dataset
uspto-grants-2011_02
Patent number
US07880001B2

Reaction notes

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