4-(4-Bromophenethyl)morpholine

4-(4-Bromophenethyl)morpholine Property

storage temp. 

Sealed in dry,Room Temperature

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

4-(4-Bromophenethyl)morpholine Chemical Properties,Usage,Production

Uses

4-(4-Bromophenethyl)morpholine is used as a reactant in the preparation of methyllysine reader protein L3MBTL3 inhibitors.

Synthesis

The general procedure for the synthesis of 4-(4-bromophenethyl)morpholine from 2-(4-bromophenyl)-1-morpholine ethanone was as follows: lithium aluminum hydride (3.35 g, 88.16 mmol, 2.00 eq.) was suspended in tetrahydrofuran (100 mL) under nitrogen protection and cooled to -30 °C. Subsequently, a solution of tetrahydrofuran (30 mL) containing 2-(4-bromophenyl)-1-morpholinoethanone (12.5 g, 44.17 mmol, 1.00 eq.) was slowly added dropwise to this suspension. The reaction mixture was stirred continuously at -30°C for 30 minutes, after which it was brought to room temperature and continued stirring for 2 hours. Upon completion of the reaction, 3.5 mL of water, 10 mL of 15% aqueous sodium hydroxide solution and 3.5 mL of water were added sequentially to quench the reaction. The insoluble solids were removed by filtration and the filtrate was extracted with ethyl acetate (1 x 150 mL). The organic layers were combined, washed successively with brine (2 × 30 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 11.5 g of 4-(4-bromophenylethyl)morpholine as a white solid in 97% yield.LC-MS analysis: (ES, m/z): 311 [M + CH3CN + H]+, 270 [M + H]+, 130, 102.

References

[1] Patent: WO2013/155338, 2013, A2. Location in patent: Page/Page column 171-172
[2] Patent: US2015/329503, 2015, A1. Location in patent: Paragraph 0704
[3] Chemical Communications, 2016, vol. 52, # 9, p. 1855 - 1858