1,2,3,4-Tetrahydropyrido[4,3-b]indole.--A riiist,ure of l-heilzoyl-3-ethosycarbi)ny1-4-piperidoiie13 (68.5 g, 0.25 niole) :tiid 6 .\' ITCl (800 nil) \?-as boiled under refliis for $ h r . .!.fter ( Y H J ~ i i l ~ . the srpnr:ifetl benzoic acid u-ar filtered, :tiit1 the filtrate \KLG tetl w ~ e r tinics ~ 1 mith ether t o remirve diss~ilvedbeiizoic ttl? :LlllLeiJll. layer I?-&< the11 eV:tplJl'&tC?dt ( l dl r e 4 r i e !vas diw)lvetl iii ethaiiol (210 ml) aiitl e a t iir:tt a t O o : plieiiylliydrazine liytirochloride (36 gr li.2.5 mole) \\-:ithen :idtied :tiid tlie rnistiirtl w:ts hoiled rirrtlrr reflux for 1 111, .Ifter cooliug, the solid W:LS filtered arid dizwlved in hot, \?-:iter, :md the solution m w iieiitralized !villi NFIj t o precipi 1 : h i i solid. Crystallization florn c~t1i:inolg:iw 17.7 :: (45:;) of I l l ? kJ:L\l.', Illl, 203 -207'. . I tl(Zl. C::tlCd fiJr C~,FII&: t;.i; 11, i.02; S, lti.;;. 1;oiiiiiI: C, 76.ti; 11, 7.23; S , 1 2 4 2-Diethylaminoethyl)-1,2,3,4-tetrahydropyrido14,341indole. --'Ti) i i solution of 1,2,3,4-tetrahydropyrido [4,3-h]indole (1.72 g. 0.01 rriole j in hot etha.iiol (20 inlj w w added 2-diethylamirioeth!.l chloride iiytirochloride (1.9 g, 0.011 niole) folloxed by KOH (0.67 g, 0.012 mcrlr) dissolved i i i the riiininiuin quantity of water. 'The mixture X I S boiled under reflux for 5ever:il hours itnd cooled, nricl t,he prec:ipitnted KC1 was filtered. The filtrate was evaprirated t ( J tiryiiess niid triturated with ROH snlut,ion, and tlie ba-e was est,r:icted iiito benzene. -4fter. dryiiig (LtgSOe) the solveiit \v:ih ev:tpor;ited to leave a viscous oil ( 2 . 3 8). This was convertciti t,o it,;; dimaleate salt ~vliii~l? i lli~etifrom iv)pri~pylalcohol: 111p 14s--14!~o. .tttuL Calrcl f i i r 61;I1231i3.26iIi4(.)-1: (;, 39.0; 11, 6.61; S : Foiriitl: ('>5D.b: 11, 6.76: N, 8.4. ,3-Dimethyl-1,2,3,4-tetrahydropyridoi4,3-b]indole was prt3p:ired from l,"-diiiieth~l-4-piperidoiie and pheiiylhgdraziiie hydrochloride a i d ( tallixed from cthyl alcohol in colorleri necdle., 11 11) 205 .5-207°. .Intrl. (':iIc~i for C131116S~:C:, 7%(l: 11, h.03; S , 14.0. I'(J1lllti c', 7 ; 7 , rT io i s, 7
l.l-Dirnethvl-3-i4-chloro~hen~l)-1,2.3,4-tetrah~dro~yrido. . - .. . _. [4,3-b]indole\T-:IS prepared from ~,,2-diriieth\.l-6-p-chlorophe~yi3-l~i~)eridviie aird Iiheiiylhydraxine hydrochloride :tnd crystallized froiii ethvl alcvhol :is Dale Tellow needles, nip 207.5-209.5".
Acknowledgments.--The author thanks Dr. D. I I)liarmacological rcsults and A h . C. S. Whyatt for t echiiical s-ihtaiirc~.
Indole Hydrazides as Potential 3Ioiioamine Oxidase Inhibitors
The pharmacological activity of hydrazine derivativcs is well known and made use of therapeutically. The :iiitihypert.ensive hydra,zinophthalazines,' analgetic and antipyretic. pyrazolones, antiphlogistic dioxopyrazolidines, thc: tuberculost,atic isonicotinoylhydrazincs, and tlie various iiioiioaniirie oxidase (AIAO) i n h i b i t o r y hydruiiic> :iiid hydra,zones are just a feiv examples. (1) E. Sclilittler, J. 1)int.y. i i i i t l .\. Alarser, I'royr. Drug K e a . , 4 , 319 (1962). ( a ) E , Jucker,driiieic. (;hem,, 71, :321 i103'3j. ( 3 ) ( a ) ,L. Pletsclier, I
