4-(4-Bromobenzyl)morpholine Chemical Properties

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

solid

color 

White

InChI

InChI=1S/C11H14BrNO/c12-11-3-1-10(2-4-11)9-13-5-7-14-8-6-13/h1-4H,5-9H2

InChIKey

KWJZFQQTDGVBOX-UHFFFAOYSA-N

SMILES

N1(CC2=CC=C(Br)C=C2)CCOCC1

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2934999090

4-(4-Bromobenzyl)morpholine Usage And Synthesis

Synthesis

Morpholine (13, 1.4 mL, 1.39 g, 16 mmol) and 4-bromobenzyl bromide (12, 1.0 g, 4 mmol) were reacted in acetonitrile (50 mL). The reaction mixture was heated to reflux for 4 hours. After completion of the reaction, water was added and extracted with dichloromethane (3 x 50 mL). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by fast column chromatography (silica gel column, 6 cm diameter, 50 mL volume, eluent n-hexane/ethyl acetate=8/2, Rf=0.19) to afford the target product 14 as a colorless solid (1.0 g, 3.9 mmol, 98% yield). The melting point of the product was 85 °C. Structural confirmation and purity analysis of the product were carried out by various analytical methods including 1H NMR, 13C NMR, IR, MS (ESI), HRMS and HPLC, which showed that the product was pure and structurally correct.

References

[1] Carbohydrate Research, 2012, vol. 359, p. 59 - 64,6
[2] Carbohydrate Research, 2012, vol. 359, p. 59 - 64
[3] Patent: WO2013/153357, 2013, A1. Location in patent: Page/Page column 18; 39
[4] Patent: US2015/45354, 2015, A1. Location in patent: Paragraph 0233-0236
[5] Patent: WO2008/154642, 2008, A2. Location in patent: Page/Page column 188-189

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