of formic acid and 1 ml of 37 aqueous formaldehyde heated under reflux for 3 hours acidified hcl and washed with ether the aqueous phase is basified 50 koh extracted with ether and concentrated final purification is accomplished employing a harrison chromatotron u00ae the major band is collected as one fraction from a 4 mm plate using a chloroform ethanol and ammonium hydroxide 85 14 1 solvent system the solvent is removed on a rotary evaporator and the residue distilled bulb to bulb at an oven temperature of 120 u00b0 125 u00b0 c 0 025 torr to give 1 36 g 59 9 of product as a clear odorless oil 1 h nmr cdcl 3 u03b4 1 45 2 64 m 11h 2 16 s 6h 3 15 3 49 m 2h 7 23 ddd 1h j 0 8 5 0 8 0 hz 7 68 dt 1h j 2 0 5 0 hz 8 46 dd 1h j 2 0 5 0 hz 8 53 br d 1h j 2 0 hz anal calc for c 14 h 23 n 3 c 72 05 h 9 94 n 18 01 employing the procedure of example ii and r s n 39 cyanomethylnornicotine as the starting material j med chem 19 1168 1976 12 0 g 83 4 of product is obtained as a clear colorless oil bp 115 u00b0 c oven 0 025 torr 1 h nmr cdcl 3 u03b4.