Diethylamine → N'-(3-(Dimethylamino)propyl)-N,N-dimethyl-1,3-propanediamine
Reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[CH3:6][N:7]([CH:9](C)C#N)[CH3:8]>[Pd]>[CH3:9][N:7]([CH3:6])[CH2:8][CH2:2][CH2:1][NH:3][CH2:4][CH2:5][CH2:6][N:7]([CH3:9])[CH3:8]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
GB-A 1,157,637, GB-A 1,157,638 and GB-A 1,157,639 disclose the reaction of 2-methylglutarodinitrile with diethylamine in the presence of hydrogen and palladium on barium sulfate or preferably palladium on carbon to form 5-diethylamino-2-methylvaleronitrile. Despite the long reaction time and a diethylamine excess of 200 mol % no tetraethyl derivative was found, although the diethylamino group reacts not only with the nitrile groups in position 5 but also with that in position 1 (ratio 4 to 1). DE-A 3,935,641 describes the synthesis of a secondary amine over a palladium catalyst. The reaction of dimethylaminopropionitrile takes place in this case with itself under hydrogenating conditions to form bis(3-dimethylaminopropyl)amine. The formation of a tertiary amine is achieved only when a spinel is used as support material which is considerably expensive to produce, and the yield is not more than 58%.
Workup
- customreacts not only with the nitrile groups in position 5
Sources & evidence
- ORD record
- ord-1ad4872ebbb34909af0cbc46013d908c
- Source dataset
- uspto-grants-1995_10
- Patent number
- US05463130
Reaction notes
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