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| {{DISPLAYTITLE:''N''-Methylconiine}} | {{DISPLAYTITLE:''N''-Methylconiine}} | ||
| {{chembox | {{chembox | ||
| | verifiedrevid = 402778508 | |||
| | Name = '''''N''-Methylconiine''' | | Name = '''''N''-Methylconiine''' | ||
| | ImageFile = nme-coniine.svg | | ImageFile = nme-coniine.svg | ||
Revision as of 12:14, 20 April 2011
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| Names | |
|---|---|
| IUPAC name 1-Methyl-2-propylpiperidine | |
| Properties | |
| Chemical formula | C9H19N |
| Molar mass | 141.258 g·mol |
| Density | (D) 0.8318 g cm at 24.3 °C (L) 0.8349 g cm at 20 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
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Infobox references
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N-Methylconiine is a poisonous alkaloid found in poison hemlock in small quantities.
Isolation and properties
The D-(+)-stereoisomer of N-methylconiine is reported to occur in hemlock in small quantities, and methods for its isolation are described by Wolffenstein and by von Braun. It is a colourless, oily, coniine-like liquid, specific rotation D +81.33° at 24.3 °C. The salts are crystalline ("B" marks one molecule of the base): the hydrochloride, B•HCl, forms masses of needles, mp. 188 °C; the platinichloride, B2•H2PtCl6, has mp. 158 °C.
The L-(-)-stereoisomer was obtained by Ahrens from residues left in the isolation of coniine as hydrobromide or by removing coniine as the nitroso-compound. It is a colourless, coniine-like liquid, bp. 175.6 °C/767 mmHg, specific rotation D -81.92° at 20 °C. The monohydrochloride crystallises in leaflets, mp. 191-2 °C; the monohydrobromide in leaflets, mp. 189-190 °C; the platinichloride in orange crystals, mp. 153-4 °C; the aurichloride in leaflets, mp. 77-8 °C; and the picrate in long needles, mp. 121-2 °C.
Synthesis
N-Methyl-D-coniine was prepared by the action of potassium methyl sulfate on coniine by Passon. Hess and Eichel have shown that D-coniine with formaldehyde and formic acid yields an active N-methyl-D-coniine, and that methyl-isopelletierine hydrazone yields N-methyl-DL-coniine when heated with sodium ethoxide at 150-70 °C.
References
- Planta and Kekulé, Annalen, 1854, 89, 150.
- Ber., 1894, 27, 2615; 1895, 28, 302
- Ber., 1905, 38, 3108; 1917, 50, 1477.
- Ber., 1902, 35, 1330; cf. Löffler and Friedrich, ibid., 1909, 42, 107.
- Ber., 1891, 24, 1678.
- Ber., 1917, 50, 1386; 1919, 52, 1622; 1920, 53, 129.