4-Methyl-1-piperazineethanol

slightly yellow low melting solid

A mixture [OF N-METHYLPIPERAZINE] (0. [0499MOL), ] [2-BROMOETHANOL] (0. [0749MOL)] and [K2CO3] (0. [0998MOL)] in 2-butanon (90mL) was stirred for [4H] at [90°C.] The cooled reaction mixture was filtered. The filtrate was evaporated. Yielding 90percent of intermediate 14. (Remark: lower yields were obtained on [A] higher scale and purification by short column chromatography was necessary).The starting material was ptepared as follows: In THF (30 ml) were added N-(2-hydroxyethyl)piperazine (500 mg, 3.84 mmol), a solution of formaldehyde (3117 mg, 38.41 mmol) and sodium cyanoborohydride (1207 mg, 19.20 mmol). The mixture was heated up to 50° C. overnight under stirring. After cooling some water was added and the mixture was extracted with DCM (3.x.). The organic layers were dried over MgSO4 and evaporated. The residue was purified over a silica plug with DCM/MeOH 9:1 as eluant to afford an oil (370 mg, Y=67percent). 2-(4-Methylpiperazin-l-yl)ethyl 4-nitrophenyl carbonate To a stirred solution of l-(2-hydroxyethyl)piperazine (26.0 g, 0.2 mol) in DMF (200 mL) was added formic acid (752 mL, 0.2 mol) and formaldehyde (16.2 g, 0.2 mol, 37percent solution in water) The reaction mixture was cautiously heated at 100 To a stirred solution of 1-(2-hydroxyethyl)piperazine (26 g, 0.2 mol) in DMF (200 mL) was added formic acid (752 mL, 0.2 mol) and formaldehyde (16.2 g, 0.2 mol, 37percent solution in water). The reaction mixture was cautiously heated at 100° C. for 2 hours then stirred overnight at room temperature. The solvent was removed in vacuo. This procedure was repeated 3 further times to give 100 g of product. The crude products were combined and distilled under vacuum to give, at 74° C., 2-(4-methylpiperazin-1-yl)ethanol (51 g, 44percent) as a colourless liquid.Analytical LCMS: (System B, R2-(4-Methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate (1) A/Preparation of N-(2-hydroxyethyl)-N'-methylpiperazine:

Molecular Weight:144.21
XLogP3:-0.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:144.126263138
Monoisotopic Mass:144.126263138
Topological Polar Surface Area:26.7
Heavy Atom Count:10
Complexity:89.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes