Ammonia → Novoldiamine
Reaction equation
[CH2:1]([N:3]([CH2:10][CH3:11])[CH2:4][CH2:5][CH2:6][C:7](=O)[CH3:8])[CH3:2].[NH3:12]>>[CH3:2][CH2:1][N:3]([CH2:4][CH2:5][CH2:6][CH:7]([NH2:12])[CH3:8])[CH2:10][CH3:11]Participants
Procedure
Novoldiamine is presently prepared by a complex synthesis. The compound is prepared commercially from 2-diethylaminoethanol and ethyl acetoacetate. The alcohol is reacted with thionyl chloride to form 2-chlorotriethylamine (A) while the acetoacetate is reacted with sodium ethoxide to provide the sodium derivative of ethyl acetoacetate (B). The initially formed compounds A and B are then condensed to yield an intermediate ester which must be hydrolyzed and then decarboxylated to provide 5-diethylamino-2-pentanone (C). This product (C) is hydrogenated in the presence of ammonia to produce the subject novoldiamine product. Other modes of preparation are known (See U.S. Pat. No. 2,365,825), but are not practiced due to the complexity of the synthesis.
Sources & evidence
- ORD record
- ord-869ad5c4503c4893b985c551dff8e20f
- Source dataset
- uspto-grants-1990_03
- Patent number
- US04910343
Reaction notes
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