4-Isobutyl-1-naphthy1acetonitrile.~ - A iriixturc of 1 - i . I i l o r o 1iietliyl-4-isohut~~lilaphthalene (46.3 g, 0.2 mole), IiCX i 1 7 3 g, 0.274 mole)? ethanol (77 ml), and n-nter (30 ml) was refluxed for 1 hr. The alcohol nx.: distilled, the residuc was extracted Experimental Section
The arysulfon!-ltliioenii(,~~r~)a~ide I 3 mmolr-) WB-: suqpeiided 5 rill of 1 .I'SaOIT. Several minutes of vigorous stirring producwl :i clear yellow wlittion. T o this was added 0.78 g iT,.G niinole.:) of methyl iodide in 1 rill of 05C;; ethaiiol. Precipitation alline product was complete i i i 13-20 m i l l . were recrystallized from et hanol-water. iii
1
\villi ether, and the soliitioii M - ~ Swashed with m-ater aiid thcir dried 1SamS04)..\iter distilling the solveni , the residue TKIS purified hy disiillitig :it 145-147' (0.4 mm), arid t h e oily product then IV:V treated with petroleum ether (bp 40-70'i l o 1s (1S.3 p, 41"; yield). On recrystallizaticili r, t h r c ~ i n i p n ~ nmelted d at 78-79' (cor). .!nul. C d c d for (-'lCTfliS: C. SG.(kj; ET, 7.67; N, 6.27. fzoiiiid: C285.4s; I T , 7.72: S , 6.13.
~-(2-Dimethylaminoethyl)-4-isobutyl-l-naphthylacetonitrile. --
This procedurt. follow the method previously descritied.4 1I ~ o l ~ u t y l - l - ~ l n ~ ) h t h \ - loiiitrile : t c t ~ i 126.8 g, 0.1 2 mole) was alkylnt(~t1 \vith 2-(S,~-tliriiethyl:irrlirio)-l-chloroet,hai~e (13.55 g, 0.126 A New Naphthylacetamide Deriva ti\ e inole), refluxiiig for 5 hr iu Iielizene (400 ml) in the prt:aeiicc' o f -odarnide (4.9 g, 0.126 mole). The product obtained w:is distillrtl :it lTO--173" ((1.4 i n l i i ) trn givc n roltrrless oil (22.9 g, 6scG yield). .Inal. C:ilrtl for C J T ~ ~ S ~C:, 81.,?8: IT. 8.90: PI', !l.+j2. Found: C, 51.04; TI, 9.01 : S , !1.:30. cu-Isopropyl-a-(2-dimethylaminoethyl)-4-isobutyl-l-naphthylacetonitrile.--Alkylatiuii of the a b ( ~ ~nitrile e (22.9 g , 0.076 niolei n-ith 2-hrorrioprop:itie ( 12.4 p, 0.101 mole) v a s perforrricJil liy refluxing for 18 lir i i i heiizrt~e(500 ml) arid i n the prrreticst. of O n i ~iiiterwt in :ttitiitiflaniriiatory tirugs tierived from 1iaphth:iloiic~,of Lyhich thus far oi-isoprop~-l-cu-(2-dimethylaniinoethyl)-l- sotiariiide (3.94 g, 0.1Ii1 n ~ d e ) . Thc distilled prnducl, hp 174t c.rilorlw~ oil f 17.6 y, 67.1C 1-i iiaphthplacetamide (1)' has been the best representative. has led u s t o synthesize t h r 4-isohut>-l derivative in analogy with 4-isot)utylpheriylac.etic arid iibufeii.ac), a productt known to w e r t a marked arislgesic and xritiinflariiiiiatory :ictiori.2 The iic'w compound, oi-is0propyl-0(-(2-diinelhyl:iniinoethyl)-4-i,~ot~uty1-l-n:tphthylacetarnide, posesses aii nrialgesic nimtioii (list iiic.11y superior t o that oi T.
Experimental Section': Tlie 1-isotiutyliiaplith~ilene required \vas ol)ttiiiietl li!. :i I I P ~ T prieral method for preparing 1-alkylnaphthalenes, which will be described in a later paper. I-Chloromethyl-4-isobutylnaphthalene.-.4 mixture of trioxymethylene (8.5 g, 0.283 mole), g1aci:rl acetic acid i l l 0 gj, and :tiihydrous HC1 ( 1 l . i g, 0.321 mole) was geiitly heated until the trioxymethplene dissolved, arid then 1-isobutylnaphthalene (40 g, 0.217 mole) m-as added and the flask carefull:- was closed arid heated for 20 hr at 65-70'. After cooling, the mixture x-as poured into water, the separated nil was extracted with benzene, and t h e resulting solutiori was \x-aqhed with water and Sa2COn and then dried (NanS04'r. The hetizeiie TV:~Qremoved in z'ac7m :knd the product was dislilled, 1,p 1:35-1:3i0 ( 0 . 3 mni), giviiig a colorless oil (35.2 g, 69.8'; yield). ilnnl. Calcd for ClsFI,,C1: C, 77.411; H , 7 . 3 6 : CY, 13.2:;. Found: C, 77.24; H, 7.28: C'1, 14.95.
Fourtd:
c:,
78.5.': IT, !i.
Derivatives of 2-Azabicyclo [2.2.2]octaric. Il*,' F H \SI;J . VILL \SI . ~ S DC~,.\IRE -4.ELLIS Jle/liciiiul (7ii;inical Reseni~chDeput.tnieni, Schering ('orpornlion, Rloo,il$eld, .Yew Jersey
12rreireil October 1.i, 1IiB.5
~
(1) a - I s o ~ ~ r o p ~ 1 - a - ( 2 - d i m e t l i ~ - l a 1 n i n o e t h ~ l ) - l - n a ~ i ~ t I 1 ~ l a cnaphe t ~ m i ~ l e , .\mitleq o i i'orniula I, related to t l i e rwpiratory stimuiatit, diethyltiicotin:rmide, were prepared. Reduction of these corntbrpramide. (a) A. Casadio, 0. Pala, E , Marazai-l'lrerti, and G. C o p r i Erpprientia, 20, 4.57 f l Q F 4 ) : (1,) 9. Casadio, G . Pala, T. Rruzzese, E. Crepounds g n w I: series of i,ompounds represented by forniul:~.: s c m z i , I:. 3Iarazzi-I~lwti,a n d G . Coppi. J . .lfd. f?/!evi.,8, 594 (1965): i c ) IT-Y. G . I'ala. A. ('asaiiio. T. I3riizzrse. I:. Creacen/i, and E. Marazsi-Lberti. i l ) i d . , 8 , 698 (1965). 185 (19titiI. idanis. 1;. E. ('IitTe. 13. 1, I , arid .I. Y. S i c i i o l w r i . .Yatui.e. 2 0 0 , 271 (1963).
