Diethanolamine → HCID 69083496, compound

Temperature

155 °C

A 100 mL two-neck flask was charged with 4-fluorobenzophenone (15.0 g; 74.9 mmol) and diethanolamine (55.1 g; 524 mmol). The flask was flushed with nitrogen, fitted with a reflux condenser and heated to 155° C. for 48 h under a gentle stream of nitrogen. Complete conversion of the starting 4-fluorobenzophenone was confirmed by TLC. After cooling to ambient temperature, the dark viscous reaction mixture was poured into water (2000 mL). The resulting suspension was thoroughly extracted with diethyl ether (6×250 mL). The aqueous phase was discarded and the organic phase was extracted with hydrochloric acid (2M, 5×200 mL). The pH of the strongly acidic aqueous phase was adjusted to 12-13 by slow addition of 35% aq. ammonia to reprecipitate the product. The aqueous phase was then reextracted with dichloromethane (3×300 mL). The crude organic extract was purified by passing through a short silica gel column (eluent: ethyl acetate). The eluted yellow solution was evaporated and the oily residue dried in vacuo to provide {4-[bis(2-hydroxyethyl)amino]phenyl}(phenyl)methanone (yellow-brown solid; 13.176 g; 62% yield).

1. customThe flask was flushed with nitrogen
2. customfitted with a reflux condenser
3. temperatureAfter cooling to ambient temperature
4. additionthe dark viscous reaction mixture was poured into water (2000 mL)
5. extractionThe resulting suspension was thoroughly extracted with diethyl ether (6×250 mL)
6. extractionthe organic phase was extracted with hydrochloric acid (2M, 5×200 mL)
7. additionThe pH of the strongly acidic aqueous phase was adjusted to 12-13 by slow addition of 35% aq. ammonia
8. extractionThe crude organic extract
9. customwas purified
10. customThe eluted yellow solution was evaporated
11. customthe oily residue dried in vacuo

ORD record

ord-8c19d15ea9ad401fb62ba7ae06a5c7a7

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09212160B2