Sodium Hydroxide → 1-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-4-methyl-piperidine-4-carboxylic acid
Reaction equation
C([O:3][C:4]([C:6]1([CH3:27])[CH2:11][CH2:10][N:9]([C:12]2[N:13]=[N:14][C:15]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:16]([CH3:19])[C:17]=2[CH3:18])[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>CCO.O>[CH2:20]([C:15]1[N:14]=[N:13][C:12]([N:9]2[CH2:10][CH2:11][C:6]([CH3:27])([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]2)=[C:17]([CH3:18])[C:16]=1[CH3:19])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 1-(6-benzyl-4,5-dimethyl-pyridazin-3-yl)-4-methyl-piperidine-4-carboxylic acid ethyl ester (0.60 g, 1.6 mmol) in EtOH (5 mL) is added sodium hydroxide (0.5 g, 13.2 mmol) in H2O (5 mL). After being stirred at 25° C. for two hr, the mixture is concentrated, and extracted with CH2Cl2 (2×10 mL) to remove impurities. The aqueous layer is acidified by 1N HCl to pH ˜5, and extracted with CH2Cl2 (6×20 mL). The combined organic solution is dried over Na2SO4, filtered and concentrated to give 1-(6-benzyl-4,5-dimethyl-pyridazin-3-yl)-4-methyl-piperidine-4-carboxylic acid (0.49 g, 89%).
Workup
- concentrationthe mixture is concentrated
- extractionextracted with CH2Cl2 (2×10 mL)
- customto remove impurities
- extractionextracted with CH2Cl2 (6×20 mL)
- dry with materialThe combined organic solution is dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a052834588bc4cd6be9c11cc09ed8586
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08481542B2
Reaction notes
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