Ammonia → HCID 10773081, compound

Temperature

60 °C

Li metal (0.63 g, 90 mmol) was added to a well stirred solution of 3-ethyl-3-methyl-1-phenylmethyl-2-piperidinone (2.08 g, 9 mmol) in dry THF (27 mL) and then liquid NH3 (180 mL) was added slowly over a period of 5 min at -78° C. The cooling bath was removed and the reaction mixture stirred for 1 h in refluxing NH3. Then the reaction mixture was heated for 5-10 min at 60° C. to evaporate NH3 leaving a white residue which was treated carefully with water (50 mL) at 0° C., and the aqueous mixture extracted with CH2Cl2 (3×50 mL). The combined organic extract was washed with brine (50 mL), dried (MgSO4), and concentrated in vacuo to give 2.81 g of a colorless viscous residue. Flash chromatography over silica gel (1% MeOH in CHCl3 -EtOAc, 1:1) afforded the lactam (1.10 g, 87% ) as a colorless solid: mp 67-69° C. (CH2Cl1-hexane).

1. additionLi metal (0.63 g, 90 mmol) was added to a well
2. customThe cooling bath was removed
3. temperaturein refluxing NH3
4. customto evaporate NH3 leaving a white residue which
5. additionwas treated carefully with water (50 mL) at 0° C.
6. extractionthe aqueous mixture extracted with CH2Cl2 (3×50 mL)
7. extractionThe combined organic extract
8. washwas washed with brine (50 mL)
9. dry with materialdried (MgSO4)
10. concentrationconcentrated in vacuo

ORD record

ord-fad71db875e44e8285e5969055deac29

Source dataset

uspto-grants-2000_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06066666