Sodium Hydroxide → 1-(4-((4-(4-Fluorophenyl)piperazin-1-yl)methyl)phenyl)cyclopropanecarboxylic acid
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4([C:24]([O:26]C)=[O:25])[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4([C:24]([OH:26])=[O:25])[CH2:22][CH2:23]4)=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
Methyl 1-(4-((4-(4-fluorophenyl)piperazin-1-yl)methyl)phenyl)cyclopropanecarboxylate (2.26 g) was dissolved in ethanol (18 ml) and a solution of sodium hydroxide (0.49 g) in water (4.6 ml) was added, and the mixture was heated at 70° C. for 2 hr. The solvent was evaporated, and the residue was dissolved in water (200 ml). The solution was neutralized with hydrochloric acid and extracted with ethyl acetate (300 ml). The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the title compound (1.73 g) as white crystals, m.p.=74-77° C.
Workup
- customThe solvent was evaporated
- dissolutionthe residue was dissolved in water (200 ml)
- extractionextracted with ethyl acetate (300 ml)
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated
Sources & evidence
- ORD record
- ord-415e75cc841c440cbd4cbe244e0f570c
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06455528B1
Reaction notes
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