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Revision as of 14:58, 25 September 2009 editEdgar181 (talk | contribs)Extended confirmed users196,325 editsm moved N-methylconiine to N-Methylconiine: capitalization of the first word in chemical names that start with a prefix is the Misplaced Pages standard← Previous edit Revision as of 15:00, 25 September 2009 edit undoEdgar181 (talk | contribs)Extended confirmed users196,325 edits minor formattingNext edit →
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{{DISPLAYTITLE:''N''-Methylconiine}}
{{chembox {{chembox
| Name = '''N-Methylconiine''' | Name = '''''N''-Methylconiine'''
| ImageFile = nme-coniine.svg | ImageFile = nme-coniine.svg
| ImageSize = 240px | ImageSize = 240px
| ImageName = N-Methylconiine | ImageName = ''N''-Methylconiine
| IUPACName = 1-Methyl-2-propylpiperidine | IUPACName = 1-Methyl-2-propylpiperidine
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
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''N''-Methylconiine is a poisonous ] found in ] in small quantities. '''''N''-Methylconiine''' is a poisonous ] found in ] in small quantities.


==Isolation and properties== ==Isolation and properties==
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<references/> <references/>


{{DEFAULTSORT:Methylconiine, N-}}
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Revision as of 15:00, 25 September 2009

N-Methylconiine
N-Methylconiine
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). Infobox references
Chemical compound

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

  1. Planta and Kekulé, Annalen, 1854, 89, 150.
  2. Ber., 1894, 27, 2615; 1895, 28, 302
  3. Ber., 1905, 38, 3108; 1917, 50, 1477.
  4. Ber., 1902, 35, 1330; cf. Löffler and Friedrich, ibid., 1909, 42, 107.
  5. Ber., 1891, 24, 1678.
  6. Ber., 1917, 50, 1386; 1919, 52, 1622; 1920, 53, 129.
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