Ammonia → HCID 10773081, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence