Sodium Hydroxide → 3-[2-(1-Isopropylcarbamoyl-piperidin-4-yl)ethoxy]-benzoic acid
Reaction equation
[CH:1]([NH:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][O:15][C:16]2[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=2)[C:19]([O:21]CC)=[O:20])[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[CH:1]([NH:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][CH2:14][O:15][C:16]2[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=2)[C:19]([OH:21])=[O:20])[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
Ethyl 3-[2-(1-isopropylcarbamoyl-piperidin-4-yl)-ethoxy]-benzoate (0.67 g, 1.8 mmol) was dissolved in ethanol (25 ml), were upon NaOH (1 N, 10 ml) was added, and the solution was stirred overnight at 20° C. The reaction mixture was concentrated in vacuo, dissolved in HCl (1 N, 25 ml) and the resulting solution was extracted with EtOAc (3×25 ml). The combined organic extracts were dried (MgSO4) and evaporated to give 0.62 of the title compound. LC-MS (m/z): 336 (M+2).
Workup
- additionwas added
- concentrationThe reaction mixture was concentrated in vacuo
- dissolutiondissolved in HCl (1 N, 25 ml)
- extractionthe resulting solution was extracted with EtOAc (3×25 ml)
- dry with materialThe combined organic extracts were dried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-3bcf2874581043b8ac404cbdbaa3ad36
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383820B2
Reaction notes
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