HCID 67355957, compound → HCID 58046537, compound

To a stirred solution of 1-ethyl-1′-methylspiro[indoline-3,4′-piperidin]-2-one (0.0046 mol) in toluene (41.6 mL) was added 2,2,2 trichloro ethyl chloroformate (6.23 mL, 0.046 mol) at 0° C. and the reaction mixture was heated at reflux for 18 h. Progress of the reaction was monitored by TLC. The reaction mixture was cooled to RT, diluted with EtOAc (2×50 mL) and washed with water (2×12 mL) and brine (12 mL). The organic portions were combined, dried over Na2SO4 and evaporated under reduced pressure. The crude product was taken up in acetic acid (12.0 mL) and Zn (4.1 g, 0.062 mol) and was added portion wise at 0° C. The reaction mixture was allowed to stir at RT for 1 h. Progress of the reaction was monitored by TLC. The reaction mixture was filtered through Celite® (diatomaceous earth) and washed with EtOAc (2×20 mL), basified using saturated NH4OH solution (15.0 mL) and extracted with DCM (2×40 mL). the organic portions were combined, dried over Na2SO4 and evaporated under reduced pressure to obtain crude 1-ethylspiro[indoline-3,4′-piperidin]-2-one (42%).

1. temperaturethe reaction mixture was heated
2. temperatureat reflux for 18 h
3. washwashed with water (2×12 mL) and brine (12 mL)
4. dry with materialdried over Na2SO4
5. customevaporated under reduced pressure
6. filtrationThe reaction mixture was filtered through Celite® (diatomaceous earth)
7. washwashed with EtOAc (2×20 mL)
8. extractionextracted with DCM (2×40 mL)
9. dry with materialdried over Na2SO4
10. customevaporated under reduced pressure

ORD record

ord-d2a33710d40f472ca0e67535d14c38ae

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09334269B2