N,N-Diethyl-1,3-propanediamine → 3-Diethylaminopropylacetamide
Reaction equation
C([N:3](CCCC)[C:4](=[O:6])[CH3:5])#N.[CH2:11]([N:13]([CH2:16][CH2:17][CH2:18]N)[CH2:14][CH3:15])[CH3:12]>O1CCCC1>[CH2:14]([N:13]([CH2:11][CH3:12])[CH2:16][CH2:17][CH2:18][CH2:5][C:4]([NH2:3])=[O:6])[CH3:15]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
12.60 g (0.09 mol) of N-cyano-N-butylacetamide are refluxed with 13.4 g (0.1035 mol) of diethylaminopropylamine in 25 ml of tetrahydrofuran for 2 hours, after which, according to investigation by gas chromatography, the educt has completely reacted to give 3-diethylaminopropylacetamide, tri-n-butylisomelamine and another component, which probably consists of butyl cyanamide. The mixture is concentrated on a rotary evaporator, and the oil which remains is left to stand at room temperature and the reaction which subsequently takes place is monitored by gas chromatography. After 5 days, the unknown component, which probably consists of butyl cyanamide, has largely reacted and has formed tributylisomelamine by trimerisation. The mixture is distilled in a bulb tube oven, first under 23.4 mbar and at a maximum temperature of 125° C. and then under 0.156 mbar and at a maximum temperature of 180° C. 6 fractions totalling 24.4 g are thereby obtained, analysis of which by gas chromatography gives a yield of 74.7% of tributylisomelamine and 96.7% of 3-diethylaminopropylacetamide. An analysis sample of tributylisomelamine, which is liquid at room temperature, can be isolated by renewed distillation of the fractions obtained under the high vacuum.
Workup
- customthe educt has completely reacted
Sources & evidence
- ORD record
- ord-17da503459de4e6abf84756e993083a3
- Source dataset
- uspto-grants-1985_08
- Patent number
- US04537946
Reaction notes
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