Acetic Acid → HCID 22643508, compound

Participants

Reaction Steps

1-Methyl-4-piperidone (566 mg, 5.0 mmol) was dissolved in 10 ml methanol and placed in 100 ml flask. 4-Chlorobenzylamine (708 mg, 5.0 mmol) was added. Mixture was stirred and Acetic acid (˜0.75 ml) was added until pH˜5. NaCNBH3 (628 mg, 10 mmol) was slowly added. Gas evolution observed. After magnetic stirring for 16 hrs methanol was partly removed on Rotavapor (40° C.). Dichloromethane, 2M NaOH and water were added until pH˜10. Phases were separated and aq. phase was then re-extracted with dichloromethane. Combined organic phases were dried over MgSO4. Concentration on Rotavapor (40° C.) yielded 1.14 g crude 47AKU-27. TLC (10% methanol in dichloromethane): Rf=0.3. HPLC-MS (Method A): M+=239.1 (MS(%)=96).

Provenance & Evidence