Morpholine → (5-Morpholin-4-YL-2-nitro-phenyl)-methanol

Temperature

110 °C

A mixture of 5-chloro-2-nitrobenzyl alcohol (1.9 g, 10.0 mmol), morpholine (0.9 mL, 10 mmol), and K2CO3 (1.4 g, 10 mmol) in DMF (20 mL) was stirred at 110° C. for 18 h. The reaction mixture was concentrated in vacuo, poured into aqueous sodium bicarbonate (NaHCO3) (5% w/v, 25 mL), and extracted with dichloromethane (25 mL). The organic extract was washed with brine (25 mL), dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography (silica gel, 4×7.5 cm, eluted with 90/10 EtOAc/MeOH) to yield a solid impure product. The residue was repurified in the same manner and the resulting solid was triturated with hexanes (10 mL) to afford the product as a yellow solid (5 mg, 2%).

1. concentrationThe reaction mixture was concentrated in vacuo
2. additionpoured into aqueous sodium bicarbonate (NaHCO3) (5% w/v, 25 mL)
3. extractionextracted with dichloromethane (25 mL)
4. extractionThe organic extract
5. washwas washed with brine (25 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated in vacuo
8. custompurified by flash chromatography (silica gel, 4×7.5 cm, eluted with 90/10 EtOAc/MeOH)
9. customto yield a solid impure product
10. customThe residue was repurified in the same manner
11. customthe resulting solid was triturated with hexanes (10 mL)

ORD record

ord-e48018380ba14c69a62eae29e497ce4b

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242115B2