Hypotensive Agents. 2-(2-Aminoethyl)-piperidine Derivatives

Minor, W.; Hoekstra, Justin B.; Fisher, Dorothea.; Sam, Joseph

doi:10.1021/jm01236a011

Cited by 4 publications

(1 citation statement)

References 9 publications

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“…The compounds listed in Table 111 also bear some structural similarity to the alkaloid lobeline (IV) (9). Table I were prepared by (a) the reaction of picolinealdehyde with acetophenones (lo), or ( b ) by the reaction of 3,4dimethoxybenzaldehyde with a-p'icoline ( l l ) , or (c) by the reaction of 2-vinylpyridine with N-methyl-phydroxyphenethylamine (V) (13, 14), or ( d ) by the Pd-C catalyzed reduction of the ethylenic groups of the products obtained in (a) and ( b ) .…”

mentioning

confidence: 99%

Phenylalkylamines

Sam

1967

Journal of Pharmaceutical Sciences

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mentioning

confidence: 99%

Phenylalkylamines

Sam

1967

Journal of Pharmaceutical Sciences

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Isoquinolines Bearing Basic Side Chains

Schuster¹,

Kathawala²

1995

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Facile and General Synthesis of 2‐, 3‐, or 4‐[(Dialkylamino)alkyl]pyridines and ‐piperidines

1993

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Reaction of (dialky1amino)alkyl chloride with picolyllithiums provides the corresponding pyridine derivatives from which the piperidines are obtained by catalytic hydrogenation.[(Dialkylamino)alkyl]pyridines and -pipendines are compounds of considerable importance in organic synthesis. Many drugs contain [(dialkylamino)alkyl]piperidines. A number of synthetic methods have been developed for the preparation of these compounds but most of them are not totally satisfactory and lack generality. Examples are the reaction of respective pyridylalkyl alcohol with hydrogen bromide and treatment of the resulting bromine derivative with secondary amine ['-3], addition of primary or secondary amina to ~inylpyridine[~-~I, or reduction and decomposition of We now report on an efficient and straightforward synthesis of pyridines 2 and piperidines 3 from 2-, 3-, or 4-picolyllithium 1 as shown in Scheme 1. Thus, reaction of alkylaminoalkyl chlorides with 1 provides derivatives 2 in good yields. These intermediates were transformed into the corresponding piperidines 3 by catalytic reduction (platinum oxide).This work was supported in part by grant NS22215 from the National Institute of Health and DE FG0582ER60649 from the Department of Energy. Experimental'H-NMR spectra: Bruker AC-300, TMS as internal standard. Picolines, 3-(diethylamino)-l-propanol, 3-(dimethylamino)-l-pro-panol, 2-(diethylamino)ethyl chloride hydrochloride, 2-(dimethylamino)ethyl chloride hydrochloride, 3-(dimethy1amino)propyl chloride hydrochloride, diisopropylamine, hexamethylphosphorous triamide (HMPT), n-butyllithium, platinum(1V) oxide, thionyl chloride, and THF were obtained from Aldrich. 4-(Dimethylamino)-1-butanol was purchased from American Tokyo Kasaei, Inc. (Tables 1 and 2). -4-[4-(Diethylamino) butyllpyridine (2g): The procedure described by Kaiser et a1.[I0] was followed. To a solution of 10.12 g (0.1 mol) of diisopropylamine in THF (100 ml) -with stirring at 0°C -a solution of n-butyllithium in hexane (0.1 mol, 2.5 M in hexane, 40 ml), was added by a syringe gradually. The mixture was then stirred for 15 min at 0°C. Hexamethylphosphoric triamide (17.92 g, 0.1 mol) in THF (40 ml) was added and the resulting solution was stirred for 15 min at 0°C. The bright yellow solution was then treated during 20 min with a solution of 4-methylpyridine (9.31 g, 0.1 mol) in THF (40 ml). Stirring was continued at 0°C for 30 min, and 3-(diethy1amino)propyl 2-(Ethylamino)ethyl

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Hypotensive Agents. 2-(2-Aminoethyl)-piperidine Derivatives

Cited by 4 publications

References 9 publications

Phenylalkylamines

Phenylalkylamines

Isoquinolines Bearing Basic Side Chains

Facile and General Synthesis of 2‐, 3‐, or 4‐[(Dialkylamino)alkyl]pyridines and ‐piperidines

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