NOTES ON SCIENTIFIC RESEARCH. 87 
Nitrogenous bodies. 
Together with G. F. Morrell, Harries’) reports on some reactions of dihydrocarvyl- 
amine, dihydroterpinylamine and carvylamine. As Morrell’) had found before, the 
oxidation of benzoyldihydrocarvylamine with ozone leads to 1-methyl-2-benzoylamino- 
4-acetylcyclohexane, the ketone properties of which were established by converting it 
into a semicarbazone (m. p. 200°) and a nitrophenylhydrazone (m. p. 252°). By ozoni- 
zation of 8-benzoyldihydroterpinylamine, trans-2-benzoylamino-1-methylcyclohexanone-4 
(m. p. 150 to 151°) was obtained, whereas the formerly described cis-2-benzoylamino-1- 
methyleyclohexanone-4 results from the «-benzoyl derivative. The semicarbazone of 
this ketone melts at 194°, the nitrophenylhydrazone at 248°. 
The authors further report on the conversion of dihydroterpinylamine into a mentha- 
diene by dry distillation of dihydroterpinylamine phosphate. Terpinene formed in 
addition to the menthadiene. 
The little investigated carvylamine, which Goldschmidt and Kisser as well as Gold- 
schmidt and Fischer*) obtained in a poor yield by reducing carvonoxime with zinc 
dust and acetic acid, has now been prepared with a much better yield by Harries and 
Morrell, who reduced carvonoxime in glacial acetic acid and alcohol with zinc dust 
under cooling with ice. The base is a colourless liquid of feeble odour and boiling at 
from 94 to 95° (12.5 mm.). The hydrochloride melts at about 220°, the «-benzoyl 
derivative at 174°. The §-benzoyl derivative (m.p.110°) had formed in only a very 
small quantity. Like dihydrocarvylamine, carvylamine combines with two molecules 
of hydrogen chloride, thus forming the hydrochloride of a chlorinated base. The di- 
hydrochloride melts at about 145°. By splitting off hydrogen chloride from the 
chlorinated base on heating with pyridine, terpinylamine forms, possibly in two iso- 
merides, and a considerable quantity of regenerated carvylamine likewise results. 
Finally, Harries and S. Smith report on some derivatives of dihydrocarvylamine. 
When this base is boiled with acetic anhydride, acetyldihydrocarvylamine (m. p. 131 
to 132°) results, which Wallach had prepared already. Oxidation of this base with 
ozone leads to 1-methyl-2-acetylamino-4-ethanoylcyclohexane melting at 193 to 194°. 
The action of anhydrous formic acid on dihydrocarvylamine leads to a body melting 
between 152 and 153°, perhaps formyldihydroterpinylamine. By the action of ethyl 
formate on dihydrocarvylamine, formyldihydrocarvylamine results (b. p. 179 to 189° at 
15 mm.), which on oxidation with ozone yields 1-methyl-2-formylamino-4-ethanoyl 
cyclohexane (m.p. 120 to 121°). The following oxalic acid derivatives of dihydrocarvyl- 
amine are worth mentioning: oxalyldihydrocarvylamine, melting at 250°, and 
semioxalyldihydrocarvylamine (m. p. 94°). Both compounds form on heating dihydro- 
carvylamine with oxalic acid. The semioxalyldihydrocarvylamine was converted into 
the semioxalyl compound of the 1-methyl-2-amino-4-ethanoylcyclohexane (m. p. 107°) 
by oxidizing it with ozone in glacial acetic acid. Carbethoxydihydrocarvylamine was 
prepared according to Claisen’s method by heating the ethereal solution of the amine 
with ethyl chlorocarbonate in the presence of dried potassium carbonate. It melts at 88°. 
It was converted into 1-methyl-2-carbethoxamino-4-ethanoylcyclohexane by ozonization 
in acetic acid. On heating the carbethoxyamino ketone with hydrochloric acid in a 
sealed tube, the hydrochloride of 1-methyl-2-amino-4-ethanoylcyclohexane (m. p. 183 to 
185°) is formed. The free base melts between 119 and 122°; b. p. 65 to 68° at 11 mm. 
*) Liehigs Annalen 410 (1915), 70. — *) Berl. Berichte 44 (1911), 2500; Report April 1912, 197. — 
*) Berl. Berichte 20 (1887), 486; 30 (1897), 2069. 
