Hydrochloric Acid → HCID 20079334, compound

The following general procedure was used to synthesize compound IV (R2 ≠H): Into a dried, 3-neck flask fitted with a mechanical stirring device, an addition funnel and a low temperature thermometer was cannulated lithium hexamethyldisilazane (1.0 M in THF, 1.1 molar equiv). The solution was cooled via a dry ice/acetone bath. A solution of N-benzoyl-4piperidone (1.0 equiv) in THF (50 mL) was added dropwise, with stirring, over thirty minutes. The solution was stirred at -72° to -68° C. for thirty minutes. Ethyl formate (2 equiv) was added all at once and the solution stirred at -70° C. for ten minutes, then at room temperature for twenty eight hours. The solution was treated with 1N HCl (200 mL) and extracted (methylene chloride and brine). The extracts were dried (MgSO4) and concentrated to yield 3-formyl-4-piperidone as an orange oil (73%).

1. customInto a dried, 3-neck flask fitted with a mechanical stirring device, an addition funnel
2. temperatureThe solution was cooled via a dry ice/acetone bath
3. stirringThe solution was stirred at -72° to -68° C. for thirty minutes
4. stirringstirred at -70° C. for ten minutes
5. waitat room temperature for twenty eight hours
6. extractionextracted (methylene chloride and brine)
7. dry with materialThe extracts were dried (MgSO4)
8. concentrationconcentrated

ORD record

ord-b1fb78459762491cae529721c1a293a8

Source dataset

uspto-grants-1995_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05405848