Sodium Hydroxide → 1-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-piperidine-4-carboxylic acid

HRID 1479970Notes

Reaction equation

HRID 1479970 reaction equation
C([O:3][C:4]([CH:6]1[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][CH:6]([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]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 671768261-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 671761271-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-piperidine-4-carboxylic acidYield 83.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1-(6-benzyl-4,5-dimethyl-pyridazin-3-yl)-piperidine-4-carboxylic acid ethyl ester (0.88 g, 2.5 mmol) in EtOH (8 mL) is added a solution of sodium hydroxide (0.8 g, 20.1 mmol) in H2O (8 mL). After being stirred at 25° C. for 2 h, 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)-piperidine-4-carboxylic acid (0.68 g, 83%).

Workup

  1. concentrationthe mixture is concentrated
  2. extractionextracted with CH2Cl2 (2×10 mL)
  3. customto remove impurities
  4. extractionextracted with CH2Cl2 (6×20 mL)
  5. dry with materialThe combined organic solution is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b57633a6bec24d708369a66294126d34
Source dataset
uspto-grants-2016_08
Patent number
US09409871B2

Reaction notes

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