Sodium Bicarbonate → N-(1H-indazol-5-ylmethyl)-4-piperidinecarboxamide

HRID 1269736Notes

Reaction equation

HRID 1269736 reaction equation
Cl.O1CCOCC1.[NH:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][NH:18][C:19]([CH:21]3[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]3)=[O:20])=[CH:14][CH:15]=2)[CH:10]=[N:9]1.C(=O)([O-])O.[Na+]>>[NH:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][NH:18][C:19]([CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[O:20])=[CH:14][CH:15]=2)[CH:10]=[N:9]1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 18447544tert-butyl 4{[(1H-indazol-5-ylmethyl)amino]carbonyl}-1-piperidinecarboxylateHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 22933995N-(1H-indazol-5-ylmethyl)-4-piperidinecarboxamideYield 9%

Procedure

A 4N-hydrochloric acid/dioxane solution (2.0 ml) was added to tert-butyl 4{[(1H-indazol-5-ylmethyl)amino]carbonyl}-1-piperidinecarboxylate (160 mg, 0.446 mmol), and the resulting mixture was stirred at room temperature for 2 hours. Then, the reaction solution was poured into a saturated aqueous sodium hydrogencarbonate solution and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The resulting residue was recrystallized from a mixture of ethanol and diethyl ether to obtain N-(1H-indazol-5-ylmethyl)-4-piperidinecarboxamide (10 mg, 9%).

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationdistilled under reduced pressure
  4. customto remove the solvent
  5. customThe resulting residue was recrystallized from a mixture of ethanol and diethyl ether

Sources & evidence

ORD record
ord-329f523df6794833a2fe812bb7dfd37e
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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