N-Methylpiperazine

N-Methylpiperazine
Names
	Preferred IUPAC name 1-Methylpiperazine
	Other names 4-Methylpiperazine; p-Methylpiperazine;
Identifiers
CAS Number	109-01-3;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1011;
ChemSpider	48024;
ECHA InfoCard	100.003.309
EC Number	203-639-5;
PubChem CID	53167;
UNII	B92I95EL9Q;
UN number	2920
CompTox Dashboard (EPA)	DTXSID4021898 ;
	InChI InChI=1S/C5H12N2/c1-7-4-2-6-3-5-7/h6H,2-5H2,1H3 Key: PVOAHINGSUIXLS-UHFFFAOYSA-N;
	SMILES CN1CCNCC1;
Properties
Chemical formula	C5H12N2
Molar mass	100.165 g·mol−1
Melting point	−6 °C (21 °F; 267 K)
Boiling point	138 °C (280 °F; 411 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H312, H314, H317, H330, H331, H332
Precautionary statements	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)	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

N-Methylpiperazine is a heterocyclic organic compound.

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]

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

^ ^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.