A Convenient Method for the Preparation of Racemic Nicotine

References

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• Alternatively, 1-nicotine (500 mg) and p-xylene were treated with an excess of potassium hydride (23% dispersion in mineral oil) at reflux temperature and with vigorous stirring for approximately one hour. The nicotine was totally racemized during this period. A similar reaction in benzene for one hour produced approximately 34% racemization. In some runs, racemization (up to 66%) varied with the dispersion of the metal hydride employed
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• All melting points were determined in open capillary tubes at a heating rate of 1°C/min. The melting (decomposition) points of this salt and the related diastereoisomeric and enantiomorphic salts (1-nicotine di-(p-toluoyl)-1-tartrate and 1-nicotine di-(p-toluoyl)-d-tartrate) (recrystallized from ethanol) all melt with decomposition in the 135–137°C range; furthermore admixtures of the various salts produced little or no change in melting point. Higher melting points (142–145°C, dec) are generally obtained at heating rates extending up to 8°C/min. The heating-rate sensitivity of the melting or decomposition points, which are not definitive indicators of purity, may explain apparent melting point discrepancies in the literature. Additionally, specific rotations of the diastereoisomeric salt forms have been found4 to be so similar that per se specific rotations of the salts fail generally to serve as adequate indicators of opitcal purity
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• Others (Hazelton International, Batch Analysis Sheet 1) have reported the resolution of nicotine via 1-nicotine bis ((di-p-toluoyl)-d-tartrate), which was described as optically pure ((α)26 D-82.5° c = 0.05 in methanol). Our 1-nicotine di-(p-toluoyl)-d-tartrate had (α)24 D -92° (c = 0.05 in methanol)
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