Methylpiperazine

N-Methylpiperazine is a heterocyclic organic compound.

N-Methylpiperazine
Names
IUPAC name
N-Methylpiperazine
Other names
  • 1-Methylpiperazine
  • 4-Methylpiperazine
  • p-Methylpiperazine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.309
EC Number
  • 203-639-5
UNII
UN number 2920
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
Safety data sheet FischerSci
GHS pictograms
GHS Signal word Danger
H226, H312, H314, H317, H318, H330, H331, H332
P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P272, P280, P284, P301+330+331, P302+352, P303+361+353, P304+312, P304+340, P305+351+338, P310, P311, P312, P320, P321, P322
NFPA 704 (fire diamond)
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
2
1
Related compounds
Related compounds
 Piperazine, 4-methylpyridine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Uses

N-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

Industrially, N-methylpiperazine is produced by reacting diethanolamine and methylamine at 250 bar and 200 °C.[5][6]

References
  1. "1-Methylpiperazine". Chemistry Dashboard. Environmental Protection Agency.
  2. "1-methylpiperazine". European Chemicals Agency.
  3. Vardanyan, Ṛuben & Hruby, Victor J. Synthesis of Essential Drugs. p. 226.CS1 maint: multiple names: authors list (link)
  4. Comins, Daniel L.; Joseph, Sajan P. (2001). "Lithium N-Methylpiperazide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rl128. ISBN 0471936235.
  5. US 4845218, "Preparation of N-Methylpiperazine", issued 1989-07-04
  6. "Catalytic synthesis of N-methylpiperazine from diethanolamine and methylamine by cyclodehydration reaction" (PDF). Indian Journal of Chemical Technology. 1 (November): 359–360. 1994.
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