Reaction equation
[NH2:1][CH:2]([CH3:5])[CH2:3][OH:4].[H-].[Na+].Cl.Cl[C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1>CN(C)C=O>[CH3:5][CH:2]([NH2:1])[CH2:3][O:4][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
6.2 g of 2-amino-1-propanol was added dropwise to a stirred mixture of 4.0 g of 60% sodium hydride and 50 ml of N,N-dimethylformamide at 5° C.~10° C. After the reaction mixture was stirred for 30 minutes, 12.5 g of 4-chloropyridine hydrochloride in limited amounts was added to the reaction mixture. The mixture was stirred for 20 hours at room temperature. After completion of the reaction, the solids in the reaction mixture were filtered off. The solvent in the filtrate was removed under reduced pressure. The residue was purified by column chromatography on silica gel to obtain 3.8 g of the desired product (yield: 30%).
Workup
- stirringThe mixture was stirred for 20 hours at room temperature
- customAfter completion of the reaction
- filtrationthe solids in the reaction mixture were filtered off
- customThe solvent in the filtrate was removed under reduced pressure
- customThe residue was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-bc6615e8435f4a96aac8a895b51be147
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05811424
Linked notes
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