Cyclohexanone → N-cyclohexylidene-(2-methylpropenylamine)

HRID 223639

Reaction equation

HRID 223639 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

4

Reactant 3

HCID 7967CyclohexanoneHCID 611384-Pentenoic acidHCID 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.

Sources & evidence

ORD record
ord-279acf50c4024af1a52e52c5c1cf3d06
Source dataset
uspto-grants-1982_10
Patent number
US04355177

Linked notes

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