Sodium Carbonate → N-Benzyl-1,4-dihydropyridine-3-carboxamide

HRID 2207144Notes

Reaction equation

HRID 2207144 reaction equation
[I-].[CH2:2]([N+:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([NH2:17])=O)[CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-:19].[Na+].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[CH2:2]([NH:9][C:10](=[O:19])[C:11]1[CH2:12][CH:13]=[CH:14][NH:17][CH:15]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24489Sodium DithioniteHCID 11393636HCID 11393636, compound

Product 1

HCID 15042636N-Benzyl-1,4-dihydropyridine-3-carboxamideYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1-benzylpyridinium-3-carboxamide iodide (1 g, 3.41 mmol) in H2O (15 mL) was added sodium carbonate (1.44 g, 13.64 mmol) and sodium dithionite (2.65 g, 12.96 mmol) at room temperature. The resulting solution was stirred under nitrogen in darkness for 15 mn. The reaction mixture was then extracted with dichloromethane. The combined organic phases were dried over Na2SO4, filtered and evaporated under reduced pressure at room temperature to afford N-benzyl-1,4-dihydronicotinamide (BNAH) (0.530 g, 73%).

Workup

  1. extractionThe reaction mixture was then extracted with dichloromethane
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure at room temperature

Sources & evidence

ORD record
ord-704b38e573fc45c08109566cb564c6d2
Source dataset
uspto-grants-2016_06
Patent number
US09376387B2

Reaction notes

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