Potassium Iodide → HCID 15376585, compound

HRID 1603967Notes

Reaction equation

HRID 1603967 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[NH:3]1.[I-].[K+].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[CH2:24]>CN1CCCC1=O>[CH2:24]([N:3]1[C:4]([CH3:9])([CH3:8])[CH2:5][CH2:6][CH2:7][C:2]1([CH3:10])[CH3:1])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 130352,2,6,6-TetramethylpiperidineHCID 28414811-Bromo-1-undecene

Product 1

HCID 15376585HCID 15376585, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

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.

Workup

  1. temperatureheated under inert atmosphere at atmospheric pressure
  2. temperaturemaintained at 120-135° C. for three hours and 100-120° C. for four hours
  3. temperatureThe slurry was cooled to room temperature
  4. custompartitioned between aqueous NaOH and hexane
  5. customto give two homogeneous liquid layers
  6. customThe upper organic layer was separated
  7. distillationdistilled below atmospheric pressure
  8. customto remove a volatile mixture
  9. customafter hexane and TMP removal
  10. distillationwas distilled at 155-164° C./3 mmHg

Sources & evidence

ORD record
ord-5a70bd2cf52644328ef72f8473eedf11
Source dataset
uspto-grants-1999_11
Patent number
US05990209

Reaction notes

Loading…