Sodium Hydroxide → HCID 58118087, compound
Reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>CO>[C:18]([C:15]1[CH:14]=[CH:13][C:12]([N:9]2[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]2)=[CH:17][CH:16]=1)([CH3:21])([CH3:19])[CH3:20]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
1-(4-Tert-butyl-phenyl)-piperidine-4-carboxylic acid ethyl ester (120 mg, 0.41 mmol, prepared in accordance with Example 48) was diluted in methanol (4 mL). An aqueous solution of sodium hydroxide (2 mL, 4M, 8.00 mmol) was then added. The resulting mixture was heated to 90° C., and then maintained at that temperature for 3 hr. After cooling to room temperature, the mixture was filtered. The filtrate was diluted with water (10 mL), and the aqueous phase was washed with ethyl acetate (10 mL). The aqueous phase was then acidified to a pH of 4 with 1 M HCl and then extracted with ethyl acetate (2×10 mL). The organic layer was collected, dried over magnesium sulfate, filtered, and concentrated under vacuum. The desired product was isolated as a solid (28 mg, 26% yield).
Workup
- temperaturemaintained at that temperature for 3 hr
- temperatureAfter cooling to room temperature
- filtrationthe mixture was filtered
- additionThe filtrate was diluted with water (10 mL)
- washthe aqueous phase was washed with ethyl acetate (10 mL)
- extractionextracted with ethyl acetate (2×10 mL)
- customThe organic layer was collected
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-bd8fbc0afbfb4275946cb3426f7b162c
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569495B2
Reaction notes
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