Ethanol → HCID 22619924, compound
Reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.C([NH2:11])C.O.[BH4-].[Na+].[CH2:15](O)[CH3:16]>C1CCCCC1>[CH2:15]([N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH2:11])=[CH:3][CH2:2]1)[CH3:16]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of pyridine-4-carboxaldehyde (26.78 g, 0.25 mole) and ethyl amine (32.2 g of a 70% water solution, 0.5 mole) were stirred for 20 min. Cyclohexane (250 ml) was added and the mixture was refluxed for 3 hrs under a Dean-Stark trap. The mixture was then concentrated in vacuo. Ethanol (250 ml) and sodium borohydride (thirteen 0.4 g tablets, 0.13 mole) were then added to the residue and mixture was stirred for 18 hrs. The mixture was concentrated in vacuo and the residue was dissolved in methylene chloride (250 ml) and filtered. The filtrate was concentrated in vacuo to give the product, N-ethyl-4-aminomethylpyridine (26.92 g, 79% which was taken on without purification.
Workup
- temperaturethe mixture was refluxed for 3 hrs under a Dean-Stark trap
- concentrationThe mixture was then concentrated in vacuo
- stirringwas stirred for 18 hrs
- concentrationThe mixture was concentrated in vacuo
- dissolutionthe residue was dissolved in methylene chloride (250 ml)
- filtrationfiltered
- concentrationThe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-c653b72d80c240229b0722661f07cd90
- Source dataset
- uspto-grants-1994_08
- Patent number
- US05338738
Reaction notes
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