Synthesis of compounds with potential central ... - ACS Publications

Central Nervous System Stimulant Activity. II. 5-Spiro-Substituted 2-Amino-2-oxazolines. M. R. Harnden and. R.. R. Rasmussen. Organic Chemistry Depart...
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KOTES

March 1970

305

TABLE I

s

SO.

1 2 3 4 >

5

6 7 8 9 All

Yield,

70

hIp,

H

64 4-CH3 70 6-CH3 68 73 4,7-(CH3)s 5-c1 65 6-C1 -58 6-Br 60 5-OCH3 66 6-OCH3 64 compou.ads &-ere analyzed for N, S and gave

Formulau

oc

(hydrochloride)

Mp, o c (picrate)

212-214 202-204 244-246 186-188 226-228 144-143 172-174 152-154 215-217

22 7-22 8 183-18.5 199-200 238-240 2.54-236 191-192 2 17-2 19 211-212 200-202

lip,

oc

CiaHisP11~02S 52-53 C14H17S302S 135-136 Ci4HiiN30zS 116-117 CiaH19?i302S 126-127 Ci3Hi4C1?;30sS 1,5.3-1,56 C13HiiClP1130zS 44-45 C13H1iBrN30BS 73-74 Ci4HnN303S 90-91 CiiHiiX;303Y 34-35 satisfactory analytical results (10.47,).

TABLE I1 -.

anesthesia------

No.

1

-1

:j

4 1

6 7 8 0 Cocaine Lidocaine Procaine

Drug concentration, Yo

0.2 0.4 0.2 0.2 0.2 0.2 0.4 0.2 0.2 0.1 0.2

75

anesthesia

100 100 100 9.5 90 100 100 93 100 96 66 100

Duration, min

26 40 52 29 70 28 38 28 39 21 14 83

Potency (cocaine = 1)

Potency (lidocaine = 1)

0 .5 0.23 0.5 0 .5 0 , ,5 0 .