tert-butyl 4-(2-broMoacetyl)piperazine-1-carboxylate

tert-butyl 4-(2-broMoacetyl)piperazine-1-carboxylate Property

Boiling point:

391.5±37.0 °C(Predicted)

Density 

1.395

storage temp. 

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

pka

-0.41±0.70(Predicted)

Appearance

White to light yellow Solid

Safety

HS Code 

2933599590

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

tert-butyl 4-(2-broMoacetyl)piperazine-1-carboxylate Chemical Properties,Usage,Production

Uses

4-(Bromoacetyl)-1-Boc-piperazine is an inhibitor of transglutaminase.

Synthesis

The reaction system was cooled to -78 °C under an inert atmosphere and bromoacetyl bromide (53.7 mmol, 1 eq.) was added slowly and dropwise to a solution of N-BOC-piperazine (53.7 mmol, 1 eq.) and triethylamine (59.1 mmol, 1.1 eq.) dissolved in dichloromethane (150 mL). The reaction mixture was stirred continuously at -78 °C for 3 h. The reaction mixture was subsequently diluted with dichloromethane (75 mL) and washed with deionized water. The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent. The crude product was recrystallized with ether, filtered and dried in vacuum to give tert-butyl 4-(2-bromoacetyl)piperazine-1-carboxylate (6q). The product was a white solid with 78% yield and melting point 23-242°C. The product was a white solid with a melting point of 23-242°C. The product was a white solid with 78% yield. Molecular weight: 307.18 g/mol. IR spectrum (KBr, cm?1): 2965(m), 1689(s), 1632(s), 1417(s), 1246(s), 1167(s), 1023(m). NMR hydrogen spectrum (250 MHz, CDCl?) δ: 3.87 (s, 2H), 3.61-3.57 (m, 2H), 3.55-3.47 (m, 4H), 3.46-3.41 (m, 2H), 1.46 (s, 9H). NMR carbon spectrum (63 MHz, CDCl?) δ: 165.5 (Cq), 154.5 (Cq), 80.5 (Cq), 46.6 (2CH?), 40.9 (2CH?), 28.4 (3CH?), 25.7 (CH?).

References

[1] Journal of the American Chemical Society, 2008, vol. 130, # 2, p. 556 - 565
[2] Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 1407 - 1413
[3] Patent: US2016/168156, 2016, A1. Location in patent: Paragraph 0510; 0511
[4] Patent: WO2014/57266, 2014, A1. Location in patent: Page/Page column 61
[5] Tetrahedron, 1998, vol. 54, # 16, p. 3999 - 4012