Potassium Iodide → HCID 15376585, compound

Participants

Reaction Conditions

Reaction Steps

2459 g of N-methylpyrrolidinone and 1013 g 2,2,6,6-tetramethylpiperidine were stirred and heated under inert atmosphere at atmospheric pressure. Granular potassium iodide (527 g) was added gradually over 45 minutes. At a slurry temperature of 112° C., 11-bromo-1-undecene (647 g) was added. The temperature was raised to 120° C. within 15 minutes, maintained at 120-135° C. for three hours and 100-120° C. for four hours. The slurry was cooled to room temperature and partitioned between aqueous NaOH and hexane to give two homogeneous liquid layers. The upper organic layer was separated and distilled below atmospheric pressure to remove a volatile mixture including hexane and tetramethylpiperidine (TMP). The portion remaining after hexane and TMP removal was distilled at 155-164° C./3 mmHg to give 704 g of 1-(10-undecenyl)-2,2,6,6-tetramethylpiperidine (98% purity by GC) as a colorless liquid. The structure was identified by NMR, GC-MS, and High Resolution MS.

Provenance & Evidence