Pyridyl methyl pyrrolidine

Im Gegensatz hierzu wird bei der Behandlung von l-Methyl-2-pyridyl-(3)-pyrrol (Ni-cotyrin) liber Palladium/Kohle bei 40-5071 bar der Pyrrol-Ring selektiv zum l-Methyl-2-pyridyl-(3)-pyrrolidin [( )-Nicotin] abgesattigt4 ... 

Nicotine. 3-tl-Methyl-2-pyrrolidinyl)pyridine 1 -methyl -2-(3 -pyridyl)pyrrolidine -pyridy] -a -N-methyl -pyrrolidine C1 HltNt mol wt 162.23. C 74.03%, H 8,70% N 17,27% From the dried leaves of Nieotiami tabacum and N. rustica where it occurs to the extent of 2 to 8%, combined with citric and malic acids. Commercial nico -tine is entirely a byproduct o the tobecco industry. Extraction procedure Gattermann, Wieland, Laboratory Methods of Organic Chemistry (New York, 24th ed-, 1937) Schwyzer,... 

Methyl-2-(3-pyridyl)pyrrolidine, nl 9 Methyl pyruvate, m3 5 5 Methyl stearate, m346... 

We now consider 7V-methyl-2-(3-pyridyl)pyrrolidine (7), also known as the alkaloid nicotine. Parallelling our discussion of coniine, we find in Kharasch and Domalski the nearly century-old enthalpy of formation for the liquid of 39 kJmol-1. Is this value plausible With (liquid, tert/R, R1, R2) necessary to transform a tertiary amine into the corresponding hydrocarbon24, we would conclude that the enthalpy of formation of liquid l-methyl-2-(3-pyridyl)cyclopentane (8, R = 3-Py) is ca —50 kJmol-1. To estimate the last datum in another way, we assume that equation 10 is essentially thermoneutral. 

Since nicotine is the major precursor to NNN in tobacco and tobacco smoke, the reaction of nicotine with sodium nitrite was studied to provide information on formation of other tobacco specific nitrosamines, especially NNK and NNA, which could arise by oxidative cleavage of the l -2 bonds or l -5 bond of nicotine followed by nitrosation (26). The reaction was investigated under a variety of conditions as summarized in Table I. All three nitrosamines were formed when the reaction was done under relatively mild conditions (17 hrs, 20 ). The yields are typical of the formation of nitrosamines from tertiary amines (27). At 90 , with a five fold excess of nitrite, only NNN and NNK were detected. Under these conditions, both NNK and NNA gave secondary products. NNK was nitrosated a to the carbonyl to yield 4-(N-methyl-N-nitrosamino)-2-oximino-l-(3-pyridyl)-1-butanone while NNA underwent cyclization followed by oxidation, decarboxylation and dehydration to give l-methyl-5-(3-pyridyl)pyrazole, as shown in Figure 4. Extensive fragmentation and oxidation of the pyrrolidine ring was also observed under these conditions. The products of the reaction of nicotine and nitrite at 90 are summarized in Table II. 

I-Methyl-2-(3-Pyridyl) Pyrrolidine 3-( 1 -Methyl-2-Pyrrolidyl) Pyridine Nicotine... 

Nicotinoids. Nicotine from tobacco was one of the earliest insecticides and was recommended for use in 1763 as a tea for the destruction of aphids (1,20). Nicotine [54-11 -3], L-l-methyl-2-(3 -pyridyl)pyrrolidine (1) (bp 247°C, d 1.009), is found in the leaves of Nicotiana tobacum and N. rustica (Solanaceae) in amounts ranging from 2 to 14%, and also is found in Duboisia hopwoodii and in Aesclepias syriaca. It occurs as the principal alkaloid along with small amounts of 12 other alkaloids of which nomicotine [494-97-3], 2-(3,-pyridyl)pyrrolidine (2) (bp 270°C, d 1.07 g/mL), and anabasine [494-52-0], l-2-(3 -pyridyl)piperidiae (3) (bp 281°C, d 1.048), are of insecticidal importance (see Alkaloids). Nomicotine occurs as both the D and L forms, the former in D. hopn oodii and the latter commonly predominating in Nicotiana. Anabasine is the chief alkaloid of Anabasis aphylla, where it occurs from 1—2% in the shoots and is found to ca 1% in Nicotianaglauca. 

Pyrrolidin l-Methyl-2-(3-pyridyl)- -1-oxid E16a, 418 (Amin-Oxidat.)... 

METHYL PYRIDYL KETONE see ABIOOO METHYL-3-PYRIDYL KETONE see ABIOOO METHYL-P-PYRIDYL KETONE see ABIOOO l-METHYL-2-(3-PYRIDYL)PYRROLIDINE see NDNOOO... 

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