N-Methylpiperazine

N-Methylpiperazine is a heterocyclic organic compound.

N-Methylpiperazine
Names
Preferred IUPAC name
1-Methylpiperazine
Other names
  • 4-Methylpiperazine
  • p-Methylpiperazine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.309
EC Number
  • 203-639-5
UNII
UN number 2920
  • InChI=1S/C5H12N2/c1-7-4-2-6-3-5-7/h6H,2-5H2,1H3
    Key: PVOAHINGSUIXLS-UHFFFAOYSA-N
  • CN1CCNCC1
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:
GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
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)
NFPA 704 four-colored diamond
2
3
1
Safety data sheet (SDS) FischerSci
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.{{cite book}}: 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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