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

HRID 2276940Notes

Reaction equation

HRID 2276940 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 1N 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-1574f3e5961b45eda01a879252d8de40
Source dataset
uspto-grants-2015_09
Patent number
US09133145B2

Reaction notes

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