Hydrochloric Acid → HCID 66751239, compound

HRID 534932Notes

Reaction equation

HRID 534932 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2([C:22]([O:24]C)=[O:23])[CH2:21][CH2:20]2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].Cl>C1COCC1>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17]([C:19]2([C:22]([OH:24])=[O:23])[CH2:21][CH2:20]2)=[O:18])[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66750880HCID 66750880, compound

Product 1

HCID 66751239HCID 66751239, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 1-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}cyclopropanecarboxylate (Example 70, 0.417 g, 1.21 mmol) in THF (5 mL) stirring at 0° C. was added 1 M lithium hydroxide solution (5 mL, 5 mmol). After 3 h, it was warmed to room temperature and kept stirring for another 3 h. The reaction mixture was acidified with 1 M hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and the solvent was evaporated in vacuum to provide 1-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}cyclopropanecarboxylic acid. (0.307 g, 77%) as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was evaporated in vacuum

Sources & evidence

ORD record
ord-1d6989bb381d43a19d78004e81bd1355
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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