Potassium Iodide → 3-[8-[4-(2,2-Diphenylethenyl)-1-piperidinyl]octyl]pyridine

HRID 1249582Notes

Reaction equation

HRID 1249582 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.[C:16]1([C:22]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:23][CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:16]1([C:22]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:23][CH:24]2[CH2:25][CH2:26][N:27]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)[CH2:28][CH2:29]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 13754500HCID 13754500, compoundHCID 137545053-(8-Chlorooctyl)pyridine

Product 1

HCID 137545063-[8-[4-(2,2-Diphenylethenyl)-1-piperidinyl]octyl]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 5-L flask equipped with a magnetic stirrer, condenser, and argon inlet tube was charged with the 191.3 g of crude, overweight 3-(8-chlorooctyl)-pyridine, 184.4 g of 4-(2,2-diphenylethenyl)piperidine, 1.0 L of N,N-dimethylformamide, 116.3 g of potassium iodide, and 74.2 g of potassium carbonate. The mixture was stirred and heated at 75° for 18 hours and then cooled to 20°. Most of the solvent was removed on a rotary evaporator at 50°/0.5 mm. The residual yellow-brown semi-solid was partitioned between 2.0 L of ether and 1.0 L of deionized water. The aqueous layer was extracted with 2×1.0 L=2.0 L of ether. The combined ether solutions were washed with 500 mL of deionized water and 500 mL of brine and dried over sodium sulfate, to which was added 20 g of Norit SG Extra charcoal. This mixture was filtered through Celite and concentrated on a rotary evaporator at 45° to an oil which solidified upon standing. The solid was triturated with 500 mL of warm hexanes. The suspension was stored overnight at -20° and filtered. The solid was washed with a total of 100 mL of cold hexanes and dried at 20°/0.1 mm over phosphorus pentoxide to give 205.9 g of 3-[8-[4-(2,2-diphenylethenyl)-1-piperidinyl]octyl]pyridine as a pale tan solid, mp 53°-54°. Liquid chromatography analysis indicated this material to be homogeneous.

Workup

  1. customA 5-L flask equipped with a magnetic stirrer, condenser, and argon inlet tube
  2. temperatureheated at 75° for 18 hours
  3. temperaturecooled to 20°
  4. customMost of the solvent was removed on a rotary evaporator at 50°/0.5 mm
  5. customThe residual yellow-brown semi-solid was partitioned between 2.0 L of ether and 1.0 L of deionized water
  6. extractionThe aqueous layer was extracted with 2×1.0 L=2.0 L of ether
  7. washThe combined ether solutions were washed with 500 mL of deionized water and 500 mL of brine
  8. dry with materialdried over sodium sulfate, to which
  9. additionwas added 20 g of Norit SG Extra charcoal
  10. filtrationThis mixture was filtered through Celite
  11. concentrationconcentrated on a rotary evaporator at 45° to an oil which
  12. customThe solid was triturated with 500 mL of warm hexanes
  13. filtrationfiltered
  14. washThe solid was washed with a total of 100 mL of cold hexanes
  15. dry with materialdried at 20°/0.1 mm over phosphorus pentoxide

Sources & evidence

ORD record
ord-922f70784dce464597c7de0e3de2a907
Source dataset
uspto-grants-1986_12
Patent number
US04632925

Reaction notes

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