18747-42-7

Basic information

• Product Name: 1-(1-Methyl-2-piperidinyl)acetone
• Synonyms: 1-(1-Methyl-2-piperidinyl)acetone;Methylisopelletierine;(+/-)-1-Methylpelletierine;1-(1-Methyl-2-piperidinyl)-2-propanone;Methylisopunicine;N-Methylisopelletierine;1-(1-methylpiperidin-2-yl)propan-2-one
• CAS NO: 18747-42-7
• Molecular Formula: C₉H₁₇NO
• Molecular Weight: 155.24
• Mol File: 18747-42-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 217℃
• Flash Point: 67℃
• Appearance: /
• Density: 0.920
• Vapor Pressure: 0.137mmHg at 25°C
• Refractive Index: 1.4674
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly)
• PKA: 9.53±0.10(Predicted)
• CAS DataBase Reference: 1-(1-Methyl-2-piperidinyl)acetone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(1-Methyl-2-piperidinyl)acetone(18747-42-7)
• EPA Substance Registry System: 1-(1-Methyl-2-piperidinyl)acetone(18747-42-7)

Safety Data

• Hazardous Substances Data: 18747-42-7(Hazardous Substances Data)

Usage

Description

This alkaloid occurs in the bark of Punica Granatum L. and was first isolated by Piccinini under the name of isomethylpelletierine. The base is an oily liquid with an alkaline reaction, miscible with H20 and optically inactive. The hydrochloride has m.p. lS6°C; the hydrobromide, m.p. lSI-2°C; the aurichloride forms rosettes of orange-yellow needles, m.p. lIS-7°C and the picrate has m.p. lS7-8°C. The alkaloid may be resolved into its optically active components. (+)-methy1isopelletierine (+)-hydrogen tartrate has m.p. 133-4°C; [α]20D + 22.7°, the corresponding figures for the antipode being m.p. 132-40c;~aH)S - 20.83° while the two hydrochlorides have [α]18D + 11.08° and - 10.64° respectively.The base gives a semicarbazone as colourless crystals, m.p. 169°C; an oxime, b.p. 1600C/12 mm and a hydrazone, b.p. lS4-SoC/29 mm. The methiodide yields cubic crystals, m.p. lS6°C. Oxidation with chromic acid in H2S04 furnishes N-methylpiperidine-2-carboxylic acid.

References

Piccinini., Gazzetta, 29, ii, 311 (1899) Hess et al., Ber., SO, 344, 1386 (1917) Hess et al., ibid, 51,741 (1918) Hess et al., ibid, 52, 964, 100S (1919)

InChI:InChI=1/C9H17NO/c1-8(11)7-9-5-3-4-6-10(9)2/h9H,3-7H2,1-2H3

Upstream product

• 6302-02-9 2-acetonylpyridine 
• 77-78-1 dimethyl sulfate 
• 87-69-4 L-Tartaric acid 
• 13070-07-0 1-methylpiperidine-2-thione 
• 49624-51-3 1-(2-N-methylpiperidyl)-propan-2-ol 
• 64-19-7 acetic acid 
• 7647-01-0 hydrogenchloride 
• 67-56-1 methanol 
• 54105-23-6 1,1'-Dimethyl-3-(2'-piperidyl)-1,4,5,6-tetrahydropyridin 
• 105-45-3 acetoacetic acid methyl ester 
• 32752-52-6 1-(N-methyl)-1,5-pentanediamine 
• 50-00-0 formaldehyd 
• 4396-01-4 isopelletierine 
• 51498-57-8 1-(1-methylpiperidin-2-yl)prop-1-yne 

Downstream Products

• 552-70-5 pseudopelletierine 
• 137595-38-1 (E)-1',2-dehydro-N-methylpelletierine 

Relevant articles and documents

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ALKALOIDS OF SOME EUROPEAN AND MACARONESIAN SEDOIDEAE AND SEMPERVIVOIDEAE (CRASSULACEAE)

Some 22 pyrrolidine and piperidine alkaloids were detected in the leafy parts of Sedum acre, S. aetnense, S. anglicum, S. brissemoreti, S. farinosum, S. fusiforme, S. lancerottense, S. melanantherum, and S. nudum.In addition to the alkaloids known from S. acre, 1-(2-pyrrolidyl)-propan-2-one and 2-monosubstituted piperidine alkaloids bearing butan-2-one, butan-2-ol, pentan-2-one and pentan-2-ol sidechains were identified.Phenylethylamine was isolated from the vegetative parts of S. album.In S. lydium, S. meyeri-johannis, and 16 species of S. series Rupestria, Aeonium, Greenovia, Jovibarba and Sempervivum no alkaloids could be detected.The results indicate a correlation between the presence of alkaloids and the major evolutionary trends in the European and Macaronesian Crassulaceae. Key Word Index: Sedum; Aeonium; Greenovia; Jovibarba; Sempervivum; Crassulaceae; pyrrolidine and piperidine alkaloids; chemotaxonomy; evolution.