128 THE SIMPLER NATURAL BASES 



Properties and Compounds of Cadaverine. 



Cadaverine or pentamethylene diamine was obtained by Ladenburg 

 [1886] by the reduction of trimethylene dicyanide, but is now 

 most easily obtained from potassium phthalimide and pentamethy- 

 lene dichloride ; the latter compound is readily formed from 

 benzoyl piperidine and phosphorus pentachloride, by von Braun's 

 method [1904]. Cadaverine is also formed in small quantity by 

 the destructive distillation of lysine (Neuberg [1905]). Cadaverine 

 is a liquid with the odour of semen and of piperidine ; b.p. 178-179 ; 

 somewhat volatile with steam, readily soluble in water and in alcohol, 

 hardly in ether ; is precipitated by alkaloidal reagents. 



The dihydro chloride, C 5 H 14 N 2 . 2HC1, needles, non-deliquescent 

 according to Gulewitsch [1894], is readily soluble in 96 per cent, 

 alcohol, sparingly in absolute alcohol. On destructive distillation it 

 yields piperidine. 



^\\Q. platinichloride, C 5 H 14 N 2 . H 2 PtCl 6 , forms orange coloured rhom- 

 bic prisms, somewhat resembling ammonium platinichloride (for details 

 see Brieger [1885, 2, p. 37]) ; they blacken at 195 and decompose at 

 215; soluble in 70*8 parts of water at 21 (Gulewitsch [1894]), in 

 113 to 114 parts of water at 12 (Udranszky and Baumann). 



The aurichloride, C 5 H 14 N 2 . 2HAuCl 4 , forms long needles and also 

 flat prisms; m.p. 186-188; fairly readily soluble in water and contain- 

 ing water of crystallisation. 



The mercurichloride, C 5 H 12 N . 2HC1 . 4HgCl 2 , prepared with excess 

 of mercuric chloride, crystallises from hot water and melts at 214*5 

 (Gulewitsch [1894]). It already loses mercuric chloride at 95. 

 Soluble in 32-5 parts of water at 21; not appreciably soluble in 

 alcohol. 



The dipicrate, C 5 H 14 N 2 . 2C 6 H 3 O 7 N 3 , forms long needles ; m.p. 221 ; 

 sparingly soluble in hot water, hardly at all in boiling alcohol. 



The dipicrolonate, C 5 H 14 N 2 . 2C 10 H 8 O 5 N 4 ^ darkens at 220 and melts 

 at 250; soluble in 7575 parts of cold water and 357 parts of boiling 

 water, 5952 parts of cold and 475 parts of boiling alcohol (about twice 

 as soluble as the putrescine salt) (Otori [1904, 3]). 



The dibenzoyl derivative, C 5 H 10 (NHCOC 6 H 5 )2, long needles, hardly 

 soluble in ether, melts at 135. 



The phenylisocyanate, C 5 H 10 (NHCONHC 6 H 5 ) 2 , is somewhat more 

 soluble in pyridine acetone than the putrescine compound and melts 

 at 207-209 (corr.). 



