RECENT WORK ON THE MORPHINE GROUP 303 



the type R . NH 2 whereby N-substituted morpholine bases are 



R.CH ' 

 obtained, or compounds of the type /O, of an aliphatic 



R.CH X 

 or alicyclic nature, may be employed. By means ol this latter 

 modification, substances which closely resemble morphine in 

 properties are obtained. 



R. Stormer 2 has worked out a second method by which 

 a morpholine derivative can be very quickly obtained — i.e. the 

 reduction of o-nitrophenacetol in boiling alcoholic solution 

 with tin and hydrochloric acid, whereby a ring is formed and 

 a methyl derivative of phenmorpholine, together with other 

 products, obtained : 



O O 



CO.CH3 



NO, 



o-Nitrophenacetol 



NH 



2-Methylphenmorpholine 



In a precisely similar manner, methylnaphthomorpholine may 

 be obtained from a-nitro-^-naphthacetol. 



One of the most interesting morpholine derivatives pre- 

 pared by Knorr 1 is naphthalanemorpholine, which was obtained 

 by the combination of tetrahydronaphthylene oxide— an ali- 

 cyclic analogue of ethylene oxide — with hydroxyethylamine. 2 

 Starting from naphthalene, the complete synthesis may be 



illustrated as follows : 



CH, 



CH 



CH, 



Dihydronaphthalene 



NH„.CH,.CH,OH 

 > 



CH HOC1 

 > 



CH 2 

 ^CH.OH 



/XH.C1 

 CH 2 



Tetrahydronaphthalene-chlorhydrin 



CH 2 OH OH 



.CH 



CH 2 H,S0 4 



CH 2 



CH, 



Tetrahydronaphthylene oxide 



CH 



CH 2 NH 



Hydroxyethylamidotetrahy'dro-^-naphthol 



CH 2 O 



CH 



CH, NH 



Naphthalane-morpholine 



1 Annalen, 307, 171 ; Ber. 32, 743. 



Annalen, 288, 89. 



