2500 CHARGE NUMBER: PROJECT TITLE: Additives Synthesi s Tobacco PERIOD COVERED: 1981 31 , January PROJECT LEADER: Seeman DATE REPORT: February 0F 11 , 1981 NICOTINE CHEMISTRY The nicotine analogue first separation isomers ha $ HPLC Thi 9Y` fully ted methodo been ucce omp ng t wi a]low major importance in tha t evemen 2-methylnicotine thylnicotine 4-me and 6-methyInic- fy puri ine ihylatiom The first nicot produced from the ne 5]HPLC eparation 0 f the key development the and stage was cenefuh and thin chromatography; very above s omers ayer 8Rce usee efforts Ted so]veni system which tedious by ine-tuning the adapted to vent subsgquently use 501 examining this method for other mixture We currently One difficult separations repreducib ifity the riddle 0 f - ab errant solved 0 f have non- dubutytesst 'Txo nicotine Rse ducts and the reaction with uM Tyhe the bigh resu] Pro When unusua reproducibility ction and observed when run deoxy enated 0 f the the etely ource two sys em comp enei Bin? the reaction products uated ami wJs va rran dihydrometanicotine and thy] cotine with ome check the the berrant product, butyllith um corrorberrani 2733*%2d Geaction thium with careful the we gn i ficant and sopropy] nicotine a t isopropyinicotine and the ma jor obta ned wa Product.7:; produc- Nicotine F (1) t-Butylithium NhcH3 NHCH3 2
CHARGE NUMBER: 2500 PROJECT TITLE: Synthesi s Tobacco Additives PERIOD COVERED: January 31 , 1981 PROJECT LEADER: Seeman DATE 0F REPORT: February 11 , 1981 NICOTINE CHEMISTRY The first separation nicotine analogue isomers ha $ been ucce fully omp ted ng HPLC methodo Thi in tha t t wi 9Y` evemen major importance a]low puri fy 2-methylnicotine 4-me thylnicotine and 6-methyInic- ne produced from the ihylatiom nicot ine The first and key stage 5]HPLC development was the eparation 0 f the above s omers thin ayer chromatography; very cenefuh and tedious efforts Ted 8Rce usee so]veni system which subsgquently adapted to use by ine-tuning the 501 vent mixture We One currently examining this method for other difficult separations have solved the riddle 0 f non- repreducib ifity 0 f - ab errant ducts and the reaction dubutytesst uM with nicotine Rse 'Txo bigh unusua Pro resu] When the Tyhe ction run and reproducibility observed when the sys em comp etely deoxy enated ource 0 f the two rran products wJs va uated ami Bin? the reaction dihydrometanicotine and thy] enei ome cotine with butyllith um check the the berrant product, we careful the Geaction corrorberrani thium with 2733*%2d nicotine a t and gn i ficant sopropy] produc- obta ned and isopropyinicotine wa the ma jor Product.7:; Nicotine NhcH3 F NHCH3 2 (1) t-Butylithium