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N methylpyrrolidine

Fluorination of N-methylpyrrole over cobalt trifluoride gives six polyfluo-rinated Af-methylpyrrolidines The same compounds and two others and perfluoro-1-methylpyrrolidme are obtained by fluorination of N-methylpyrrolidine. The yields of the individual products are low [75] (equation 8)... [Pg.125]

The dimer of 1-methyl- -pyrroline (39) was obtained by reduction of N-methylpyrrole with zinc and hydrochloric acid (132) and, together with the trimer, by mercuric acetate dehydrogenation of N-methylpyrrolidine (131). J -Pyrroline-N-oxides form dimers in a similar manner (302). Treatment of 1,2-dimethyl-zl -piperideine with formaldehyde, producing l-methyl-3-acetylpiperidine (603), serves as an example of a mixed aldol reaction (Scheme 18). [Pg.298]

Azelastine (107) is an antiallergic/antiasthmatic agent prepared from 4-chlorobenzyl-2 -car-boxyphenylketCHie (105) by condensation with hydrazine to give the phthalazinone (106) followed by reaction of the sodium salt of this last with 2-(2-chloroethyl)-N-methylpyrrolidine (presumably involving nucleophilic ring expansion of the bicyclic quaternary salt putatively formed as a first product) to complete the synthesis [30]. [Pg.152]

Krapcho and Vivelo have described a new formal total synthesis of tropinone (124) and ( )-cocaine (98) (94). Cycloaddition of IV-methylpyrrole (182) and acetylenedicarboxylic acid leads to 183, which is hydrogenated to 184. The diacid mixture 184 is refluxed in MeOH/HCl to yield the diester mixture 185. Addition of this to an excess of metallic sodium in liquid ammonia at — 78°C leads to the N-methylpyrrolidine derivative 186 (cf. 95), whose diethyl analog 147 has earlier been converted to tropinone (124) and (+)-cocaine (98) (78-80) (Scheme 13). [Pg.39]

GC analysis for methanol, 1-propanol, 1-butanol, pyrrolidine, N-methylpyrrolidine, 2-pynolidinone, N-methyl-2-pyrrolidinone, gamma-butrolactone, dimethylsuccinate, and N-butyl-2-pyrrolidinone was performed with a Hewlett-Packard Model 5890 Gas Chromatograph equipped with a 30-meter, 0.53 mm I.D., 0.50-micron film, Nukol capillary column (Supelco, Bellefonte, PA) and a flame ionization detector (FID). [Pg.149]

Figure 15.4 The synthesis of N-methylpyrrolidine-Cso proceeds through an intermediate azomethine ylide by the reaction of N-methylglycine plus formaldehyde upon heating... Figure 15.4 The synthesis of N-methylpyrrolidine-Cso proceeds through an intermediate azomethine ylide by the reaction of N-methylglycine plus formaldehyde upon heating...
Fell and Bari (89) also studied the rhodium-catalyzed reaction. A rho-dium-N-methylpyrrolidine-water catalyst system was very effective for producing the propane-1,2-diol acetate directly. The best yields (>90%) of product of about 9 1 alcohol aldehyde ratio were obtained in the region of 95°-l 10°C. This range was very critical, as were other reaction parameters. Rhodium alone gave the best yield of aldehyde (83%) at 60°C. Triphenylphosphine as cocatalyst induced the decomposition of the aldehyde product. [Pg.43]

R = R1 = Et, R2 = H,R4 = H,Me)in 10% and 55% yields. Under similar conditions, N-methylpyrrolidine-2-thione and pyrrolidine-2-thione failed to react [84IJC(B)1176, 84SC533]. [Pg.121]

CHLORO-2-METHYLBUTANE N-METHYLPYRROLIDINE PIPERIDINE tert-BUTYLFORMAMIDE ISOPENTANE NEOPENTANE n-PENTANE... [Pg.37]

Nicotine is an oily, volatile liquid and is the principal alkaloid found in tobacco Nicotiana tabacum). It can be seen to be a combination of two types of heterocycle, i.e. the aromatic pyridine and the non-aromatic N-methylpyrrolidine. [Pg.412]

N-methylpyrrolidine gave a small amount (5%) of unchlorinated compound 215 with the pentathiepin ring fused across the 2,3-pyrrole bond and N-ethylpyrro-lidine gave a higher percentage (23%) of product 216 fused similarly to the former but chlorinated in the free a-position of the pyrrole (Scheme 113). [Pg.216]

In contrast to cobalt, rhodium permits a one-step oxo alcohol synthesis in the presence of certain monomeric and polymeric amines (8, 9, 10). Included in this group are triethylamine, N-alkylpiperidines, N-methylpyrrolidine, and N,N-dimethylbenzylamine (DMBA). Initial kinetic data on this amine-promoted alcohol synthesis (under severe reaction conditions) have been reported by B. Fell and coworkers (II), but no attempt has been made to characterize the catalytic species in the reaction cycle. [Pg.250]

Finally, the LDA deprotonation of amine N-oxides has been reported to generate azomethine ylides that can be trapped in [2 + 3] cycloadditions with simple alkenes.126 For example, N-methylpyrrolidine N-oxide (137) reacts with LDA in the presence of cyclopentene to give adduct (139 Scheme 31). A variety of other N-oxides behave similarly. Interestingly, there are no examples published to date where nonstabilized azomethine ylides generated by the desilylation procedure can be trapped by simple, unactivated alkenes. It is not clear whether these discrepancies are due to some fundamental difference in the reactive intermediate being generated, or whether the differences in environment are responsible for differing behavior. Further work is needed to establish this point. [Pg.1089]

Nicotine (C10H14N2, beta-pyridyl-alpha-N methylpyrrolidine), a highly poisonous alkaloid, is first isolated from tobacco. [Pg.13]

Nicotine (C10 H14 N2, beta-pyridyl-alpha-N methylpyrrolidine) is a very poisonous, water- and lipid-soluble, liquid alkaloid with a burning taste. It is colorless, but turns brown and takes on the odor of tobacco upon exposure to air. First isolated in 1828, it is used as an insecticide in agriculture, and as a killer of parasites in veterinary medicine. [Pg.365]

A mixture of 7-[(Z)-2-ethoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-iodomethyl-3-cephem-4-carboxilate (4.5 g, 4.83 mmoles) and N-methylpyrrolidine (0.65 ml, 6.28 mmoles) in CH2CI2 (45 ml) was stirred at room temperature for 20 min. Ether (300 ml) was added to the mixture to separate the quaternary salt of the blocked cephalosporin, which was collected by filtration and treated with 90% trifluoroacetic acid (TFA) (40 ml) at room temperature for 1 hour. The mixture was then evaporated under reduced pressure below 20°C. The residue was triturated with ether to give the TFA salt of 7-[(Z)-2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[(l-methyl-l-pyrrolidinium)methyl]-3-cephem-4-carboxylate (2.40 g), which was dissolved in methanol (5 ml) and treated with 1 M solution of sodium-2-ethylhexoate in ethyl acetate (8 ml) at room temperature for 30 min. After the addition of ethyl acetate (100 ml), the precipitate (1.94 g) formed was collected by filtration. HPLC analysis showed that the crude product was 7% pure with a 1 8 ratio of the S3 isomer to the S2 isomer. Purification of the product by HPLC was repeated three times (Lichrosorb RP-18, eluted with 5% aqueous methanol or 0.01 M ammonium phosphate buffer (pH 7.2 containing 5% of methanol) to give 35 mg (1.5%) of the title product as a colorless powder of 7-[(Z)-2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[(l-methyl-l-pyrrolidinium)methyl]-3-cephem-4-carboxylate. Estimated purity (by HPLC) 90%. M.p. 150°C (dec.). [Pg.884]

A mixture of the appropriate phenyl vinyl sulfone, tri-o-tolylphosphine, palladium (II) acetate, triethlamine and (R)-5-bromo-3-(N-methylpyrrolidinylmethyl)-lH-indole in anhydrous acetonitrle was heated at reflux under nitrogen. The resultant reaction mixture was evaporated under reduced pressure, and the residue was column chromatographed using silica gel and elution with methylene chloride/absolute ethanol/ammonia to afford the (R )-5-trans-(2-phenylsulfonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-lH-indole. [Pg.1425]

The salt eletriptan hydrobromide may be produced by reaction of the (R)-5-(2-phenylsulfonylethyl)-3-(N-methylpyrrolidin-2-ylmethyl)-lH-indole with hydrobromic acid. [Pg.1426]


See other pages where N methylpyrrolidine is mentioned: [Pg.36]    [Pg.39]    [Pg.604]    [Pg.187]    [Pg.1274]    [Pg.16]    [Pg.367]    [Pg.158]    [Pg.11]    [Pg.64]    [Pg.92]    [Pg.119]    [Pg.157]    [Pg.183]    [Pg.37]    [Pg.1535]    [Pg.279]    [Pg.238]    [Pg.239]    [Pg.366]    [Pg.367]    [Pg.368]    [Pg.369]    [Pg.377]    [Pg.1138]    [Pg.25]    [Pg.2491]    [Pg.183]    [Pg.147]    [Pg.2]    [Pg.452]   
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See also in sourсe #XX -- [ Pg.56 ]

See also in sourсe #XX -- [ Pg.337 ]

See also in sourсe #XX -- [ Pg.148 ]




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