Pyrrolidine hydrochloride

To a solution of previously dried l-[[2-carboxy-3-(2-dimethylaminoethyl)-5-indolyl]methanesulphonyl]-pyrrolidine (1.6 g 0.0442 moles) in anhydrous quinoline (75 ml) and under atmosphere of nitrogen, cuprous oxide (160 mg 0.0011 moles) was added. The reaction mixture was heated to 190°C for 15 minutes, stirred to room temperature, poured into a mixture of 1 N hydrochloric acid (150 ml) and ethyl acetate (50 ml), shaken and decanted. The aqueous solution was washed several times with ethyl acetate, then solid sodium bicarbonate was added until pH = 7.8, and washed with n-hexane to eliminate the quinoline. The aqueous solution was made alkaline with solid potassium carbonate and extracted with ethyl acetate. The organic solution was dried (Na2S04), the solvent removed under reduced pressure when a dark oil was obtained (1.3 g yield 92%). This product was purified by column chromatography with silica gel and methylene chloride ethanol ammonium hydroxide (60 8 1) as eluent and a white foam (0.8 g) of l-[[3-(2-dimethylaminoethyl)-5-indolyl]methanesulphonyl]-pyrrolidine was obtained. To a solution of the above product (0.8 g) in acetone (30 ml), a few drops of hydrogen chloride saturated dioxan solution, were added. The precipitated solid was collected by filtration, washed with acetone and dried to give l-[(3-(2-(dimethylamino)ethyl)-5-indolyl)methanesulphonyl]-pyrrolidine hydrochloride (0.75 g). Melting point 218°-220°C. 

Chemical Name l-(2-N-Benzylanilinoethyl)pyrrolidine, hydrochloride Common Name Histapyrrodinum Structural Formula ... 

Pyrrolidine Acetyl chloride A/-Acetylpyrrolidine (79%) Pyrrolidine hydrochloride... 

Chlorobutyronitrile heated 10 hrs. at 120° with a soln. of anhydrous NHg in abs. ethanol under autogenous pressure in a stainless-steel autoclave 2-imino-pyrrolidine hydrochloride. Y 83%. F. e., also with methylamine, s. E. J. Moriconi and A. A. Cevasco, J. Org. Chem. 33, 2109 (1968). 

Beckmann JS, Siripurapu KB, Nickell JR et al (2010) The novel pyrrolidine Nor-Lobelane analog UKCP-110 [cis-2,5-di-(2-phenetyl)-pyrrolidine hydrochloride] inhibits VMAT2 function, methamphetamine-evoked dopamine release, and methamphetamine self-administration in rats. J Pharmacol Exp Ther 335 841-851. doi 10.1124/jpet.ll0.172742... 

Reagent and conditions i, ethyl formate, MeONa, MeOH ii, sulfonylbenzene chloride, DMF iii, methylthioglycolate, MeONa, MeOH iv, dimethoxy THF, 4-chloropyridine hydrochloride, dioxane v, pyrrolidine vi, (a) POCI3, (b) 10% NaOH... 

Reagent and conditions i, diethyl chloromalonate, DMF ii, DBN, MeOH iii, AcOH, H2O iv, AcONa, diethyl aminomalonate HCI, MeOH/H20 v, MeONa, MeOH vi, 2,5-dimethoxyTHF, 4-chloropyridine hydrochloride, dioxane vii, pyrrolidine viii, (a)POCI3, (b) 10%NaOH... 

The synthesis of the rare amino acid 3-hydroxy-4-methylproline (8)3 involves an aldol reaction of the oxazoiidinone 5 with methacrolein to provide the a-bromo-0-hydroxy adduct 6. Azide displacement and removal of the chiral auxiliary gives 7. On treatment with dicyclohexylborane, 7 undergoes hydroboration-cycloalkyl-ation to provide, after hydrolysis, the methyl ester hydrochloride (8) of (2S,3S,4S)-3-hydroxy-4-methylproline in >97% de. This cycloalkylation should be a useful route to cyclic amino acids as well as pyrrolidines. 

Type iii-a The formation of (66) is found in the electrolysis of partially neutralized trifluoroacetic acid in the presence of diallylamine (78). It provides the crystalline hydrochloride of ds-3,4-bis-(2,2,2-trifluoroethyl)pyrrolidine (79) in 8% yield (Scheme 28) [101]. 

Nuclear magnetic resonance (n.m.r.) studies have revealed that 4-amino-4-deoxy-L-xylose,35,350 4-amino-4,5-dideoxy-L-xylose,356 and 4-amino-4-deoxy-D-glucose34 (40) exist as equilibrium mixtures for example, of the pyrrolidine 40, the pyrroline 39 formed by its dehydration, and a dimer (41), the equilibrium lying strongly towards the last. Similar studies have shown that the hydrochlorides of 4-amino-... 

These alkaloids contain pyrrole or modified pyrrole, e.g. pyrrolidine, ring system. The simplest example of this class is nicotine. A pyrrolidine ring is the central structure of the amino acids proline and hydroxyproline. These alkaloids are also found in many drug preparations, e.g. procyclidine hydrochloride, which is an antichohnergic drug mainly used for the treatment of drug-induced Parkinsonism, akathisia and acute dystonia. 

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