N-Methylpiperazine is a heterocyclic organic compound.
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| Names | |
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| Preferred IUPAC name
1-Methylpiperazine | |
Other names
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.003.309 |
| EC Number |
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PubChem CID
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| UNII | |
| UN number | 2920 |
CompTox Dashboard (EPA)
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| Properties | |
| C5H12N2 | |
| Molar mass | 100.165 g·mol−1 |
| Melting point | −6 °C (21 °F; 267 K)[1] |
| Boiling point | 138 °C (280 °F; 411 K)[1] |
| Hazards | |
| GHS labelling: | |
   
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| Danger | |
| H226, H312, H314, H317, H330, H331, H332 | |
| P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P272, P280, P284, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P311, P312, P320, P321, P322, P333+P313, P363, P370+P378, P403+P233, P403+P235, P405, P501 | |
| NFPA 704 (fire diamond) | |
| Safety data sheet (SDS) | FischerSci |
| Related compounds | |
Related compounds
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Piperazine, 4-methylpyridine |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Uses
editN-Methylpiperazine is a common building block used in organic synthesis.[2] For example, N-methylpiperazine is used in the manufacture of various pharmaceutical drugs including cyclizine,[3] meclizine, and sildenafil.
The lithium salt, lithium N-methylpiperazide, is used as a reagent in organic synthesis for protection of aryl aldehydes.[4]
Synthesis
editIndustrially, N-methylpiperazine is produced by reacting diethanolamine and methylamine at 250 bar and 200 °C.[5][6]
References
edit- ^ a b "1-Methylpiperazine". Chemistry Dashboard. Environmental Protection Agency.
- ^ "1-methylpiperazine". European Chemicals Agency.
- ^ Vardanyan, Ṛuben & Hruby, Victor J. Synthesis of Essential Drugs. p. 226.
{{cite book}}: CS1 maint: multiple names: authors list (link) - ^ Comins, Daniel L.; Joseph, Sajan P. (2001). "Lithium N-Methylpiperazide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rl128. ISBN 0471936235.
- ^ US 4845218, "Preparation of N-Methylpiperazine", issued 1989-07-04
- ^ "Catalytic synthesis of N-methylpiperazine from diethanolamine and methylamine by cyclodehydration reaction" (PDF). Indian Journal of Chemical Technology. 1 (November): 359–360. 1994.