Morpholine → 4-(3-bromobenzyl)morpholine

Temperature

27.5 °C

To a stirred solution of morpholine (0.5 g, 5.8 mmol) in acetonitrile (5 ml) was added K2CO3 (2.4 g, 17.44 mmol), followed by 3-bromobenzyl bromide (1.45 g, 5.8 mmol) at 0° C. and the reaction mixture was stirred at 20-35° C. for 16 h. The progress of the reaction was monitored by TLC. After 16 h of stirring, the mixture was diluted with water (50 ml) and extracted with ethyl acetate (2×50 ml). The combined organic layers were washed with brine (50 ml), followed by drying over anhydrous Na2SO4 and filtering. The filtrate was rotary evaporated to get residue which was purified by column chromatography using a mixture of 5% ethyl acetate/hexane as an eluent to get the desired compound as a white solid (700 mg, 35%). 1H NMR (400 MHz, DMSO-d6) δ 7.26 (d, J=8.3 Hz, 2H), 7.19-7.15 (m, 2H), 5.18 (s, 2H), 3.56 (t, J=4.6 Hz, 4H), 2.58 (t, J=4.4 Hz, 4H).

1. stirringAfter 16 h of stirring
2. extractionextracted with ethyl acetate (2×50 ml)
3. washThe combined organic layers were washed with brine (50 ml)
4. dry with materialby drying over anhydrous Na2SO4
5. filtrationfiltering
6. customThe filtrate was rotary evaporated
7. customto get residue which
8. customwas purified by column chromatography
9. additiona mixture of 5% ethyl acetate/hexane as an eluent

ORD record

ord-7fbeda166fc348788d9c9ff3716fe9b8

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09062002B2