Reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=[O:6].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[CH2:13]([NH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=[O:6])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of N-(2-aminoethyl)pyridine-3-carboxamide (26.5 g.) and benzaldehyde (16.35 ml.) in ethanol (220 ml.) was kept for 48 hours. A small quantity of solid was removed by filtration. Sodium borohydride (6.1 g.) was then added to the filtrate which was stirred for 1 hour. Glacial acetic acid was then added cautiously until the solution was neutral. The solution was diluted with water (100 ml.) and basified with 2M sodium hydroxide. The mixture was extracted with ethyl acetate (3×200 ml.) and the extracts washed with saturated brine, dried (Na2SO4) and evaporated. The residue was purified by chromatography on a column of Florisil (200 g.), eluting with ethyl acetate, to yield N-[2-(benzylamino)ethyl]pyridine-3-carboxamide (29.5 g.) as a pale brown oil.
Workup
- customA small quantity of solid was removed by filtration
- additionSodium borohydride (6.1 g.) was then added to the filtrate which
- additionGlacial acetic acid was then added cautiously until the solution
- additionThe solution was diluted with water (100 ml.)
- extractionThe mixture was extracted with ethyl acetate (3×200 ml.)
- washthe extracts washed with saturated brine
- dry with materialdried (Na2SO4)
- customevaporated
- customThe residue was purified by chromatography on a column of Florisil (200 g.)
- washeluting with ethyl acetate
Sources & evidence
- ORD record
- ord-7a9c8347d88d4f9090754c71dd962048
- Source dataset
- uspto-grants-1986_02
- Patent number
- US04568691
Linked notes
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