Ammonium formate → HCID 86616749, compound

Ammonium formate (1.38 g, 22 mmol) and 10% Pd/C (230 mg, 0.2 mmol) are added to a solution of 1-(2,2,2-trifluoroethyl)-4-(4-nitrophenyl)piperidine (1.26 g, 4.4 mmol) in EtOH (10 mL) and EtOAc (10 mL). The suspension is heated at reflux for 24 hours, adding further portions of ammonium formate (2 g) after 4 h and 8 h. The mixture is filtered through celite and evaporated to afford an orange solid. This is partitioned between DCM (40 mL) and water (20 mL) and the layers separated. The aqueous phase is extracted with DCM (2×20 mL) and the combined organic layers are dried over MgSO4 and evaporated under reduced pressure to afford N-{4-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]phenyl}formamide as a pale orange solid (980 mg).

1. temperatureThe suspension is heated
2. temperatureat reflux for 24 hours
3. custom8 h
4. filtrationThe mixture is filtered through celite
5. customevaporated
6. customto afford an orange solid
7. customThis is partitioned between DCM (40 mL) and water (20 mL)
8. customthe layers separated
9. extractionThe aqueous phase is extracted with DCM (2×20 mL)
10. dry with materialthe combined organic layers are dried over MgSO4
11. customevaporated under reduced pressure

ORD record

ord-91963dc6898f45e797118ecedb347db6

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173656B2