Cyclohexanone → N-cyclohexylidene-(2-methylpropenylamine)

Reaction equation

C=CCCC(O)=O.[C:8]1(=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[CH2:15]([NH2:19])[C:16](=[CH2:18])[CH3:17]>>[C:8]1(=[N:19][CH:15]=[C:16]([CH3:18])[CH3:17])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

Reactant 3

HCID 7967Cyclohexanone

HCID 611384-Pentenoic acid

HCID 761412-Methylallylamine

Product 1

HCID 20436157N-cyclohexylidene-(2-methylpropenylamine)

Procedure

The procedure described in Example 1(a) is repeated, except that 302.5 g (2 mols) of N-cyclohexylidene-(2-methylpropenylamine) and 250 g (4.62 mols) of 1,3-butadiene are used. Distillation yields 382 g (1.48 mols) of 3,3-dimethyl-12,12-pentamethylene-1-aza-1,5,9-cyclododecatriene; boiling point 96° C./4 Pa; nD20 =1.5116. The N-cyclohexylidene-(2-methylpropenylamine) was prepared from cyclohexanone and methallylamine, with subsequent isomerisation of the reaction product with potassium tert.-butylate; boiling point 96° C./1,700 Pa; nD20 =1.5160.