4-N-Boc-2-Methyl-piperazine Chemical Properties

Boiling point:

268.7±15.0 °C(Predicted)

Density 

0.997±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

Chloroform, DMSO, Ethyl Acetate

pka

8.52±0.40(Predicted)

form 

Oil

color 

Clear Colourless

InChI

InChI=1S/C10H20N2O2/c1-8-7-12(6-5-11-8)9(13)14-10(2,3)4/h8,11H,5-7H2,1-4H3

InChIKey

FMLPQHJYUZTHQS-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCNC(C)C1

CAS DataBase Reference

120737-59-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

36/37/38-50

Safety Statements 

26-36/37/39-61-37

RIDADR 

UN3077

HS Code 

29335990

4-N-Boc-2-Methyl-piperazine Usage And Synthesis

Chemical Properties

Clear Colourless Oil

Uses

4-N-Boc-2-methylpiperazine is a boc protetcted piperazine derivative used in the preparation of prazosin-related compounds with blocking activity toward α-adrenoreceptors.

Synthesis

General procedure for the synthesis of 4-tert-butoxycarbonyl-2-methylpiperazine from di-tert-butyl dicarbonate and 2-methylpiperazine: 1) Di-tert-butyl dicarbonate (21.7 g) was slowly added to a solution of 2-methylpiperazine (10.0 g) in methanol (200 mL) at room temperature, followed by continuous stirring of the reaction mixture for 24 hours. Upon completion of the reaction, the methanol solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography (eluent: chloroform-methanol mixed solvent) to finally obtain tert-butyl 3-methylpiperazine-1-carboxylate as a colorless oily product (19.3 g, 96.5% yield). The product was characterized by 1H-NMR (300 MHz, CDCl3): δ1.04 (3H, d, J=6.24 Hz), 1.46 (9H, s), 2.39 (1H, br s), 2.70-2.77 (3H, m), 2.94 (1H, br s), 3.93 (2H, br s). Mass spectrometry analysis (FAB) showed the molecular ion peak M/Z: 201 (M+H)+.

References

[1] Patent: US2003/153556, 2003, A1
[2] Patent: EP1621537, 2006, A1. Location in patent: Page/Page column 33
[3] Patent: WO2016/168619, 2016, A1. Location in patent: Paragraph 00286
[4] Patent: EP1548010, 2005, A1. Location in patent: Page/Page column 19
[5] Journal of Medicinal Chemistry, 2016, vol. 59, # 11, p. 5432 - 5448

4-N-Boc-2-Methyl-piperazine(120737-59-9)Related Product Information

• Butyl acetate
• Methyl acrylate
• Methyl salicylate
• RESMETHRIN
• tert-Butyldimethylsilyl chloride
• Tribenuron methyl
• Piperazine
• Cyhalofop-butyl
• Diethylene glycol monobutyl ether
• Buprofezin
• METSULFURON METHYL
• 2-Methylpiperazine
• 2-Butoxyethanol
• Methyl acetate
• 1-Methylpiperazine
• Kresoxim-methyl
• BUTYL OLEATE
• Butyl acrylate