Sodium Hydroxide → N-(2-pyrazinylmethyl)-3-chloropropionamide
Reaction equation
[OH-].[Na+].Cl.[NH2:4][CH2:5][C:6]1[CH:11]=[N:10][CH:9]=[CH:8][N:7]=1.[Cl:12][CH2:13][CH2:14][C:15](Cl)=[O:16]>O>[N:7]1[CH:8]=[CH:9][N:10]=[CH:11][C:6]=1[CH2:5][NH:4][C:15](=[O:16])[CH2:14][CH2:13][Cl:12]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To an aqueous solution of sodium hydroxide (2.31 g) in water (30 ml) was added 2-aminomethylpyrazine hydrochloride (7.0 g) under ice cooling, to which 3-chloropropionylchloride (5.05 g) and solution of sodium hydroxide (2.31 g) in water (30 ml) were simultaneously added dropwise over 30 minutes under stirring. The mixture was stirred for 1 hour at room temperature, followed by extraction with ethyl acetate-THF (1:1, 100 ml×2). The aqueous layer was subjected to salting out with sodium chloride, followed by extraction with ethyl acetate-THF (1:1, 100 ml×2). The organic layers were combined and dried over magnesium sulfate, followed by concentration under reduced pressure. The concentrate was subjected to column chromatography [carrier: silica gel, 200 g; developing agent: ethyl acetate→ethyl acetate-ethanol (4:1)]. The eluent was concentrated and the resulting solid was washed with hexane to give the title compound (4.50 g) as colorless solid product.
Workup
- stirringThe mixture was stirred for 1 hour at room temperature
- extractionfollowed by extraction with ethyl acetate-THF (1:1, 100 ml×2)
- extractionfollowed by extraction with ethyl acetate-THF (1:1, 100 ml×2)
- dry with materialdried over magnesium sulfate
- concentrationfollowed by concentration under reduced pressure
- concentrationThe eluent was concentrated
- washthe resulting solid was washed with hexane
Sources & evidence
- ORD record
- ord-07329e5bb77e42fcbde3bfeb5120ef83
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06174877B1
Reaction notes
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