Potassium Iodide → HCID 22850948, compound

HRID 487218Notes

Reaction equation

HRID 487218 reaction equation
[CH3:1][C:2]1([CH3:17])[C@H:7]2[CH2:8][C@@H:3]1[CH2:4][CH2:5][C@H:6]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15]Cl.[CH3:18][NH:19][CH2:20][CH2:21][C:22]1[CH:31]=[CH:30][C:27]([O:28][CH3:29])=[C:24]([O:25][CH3:26])[CH:23]=1.C(N(CC)CC)C.[I-].[K+]>C(#N)C.ClCCl>[CH3:1][C:2]1([CH3:17])[C@H:7]2[CH2:8][C@@H:3]1[CH2:4][CH2:5][C@H:6]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][N:19]([CH2:20][CH2:21][C:22]1[CH:31]=[CH:30][C:27]([O:28][CH3:29])=[C:24]([O:25][CH3:26])[CH:23]=1)[CH3:18]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 8471TriethylamineHCID 77039N-MethylhomoveratrylamineHCID 22850938HCID 22850938, compound

Product 1

HCID 22850948HCID 22850948, compoundYield 42.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

7 g 4-[2-((1S,2S,5S)-6,6-dimethylbicyclo[3,1,1]hept-2-yl)-ethoxy]-butyl chloride, 5.8 g N-methyl-homoveratrylamine, 4 ml triethylamine and a catalytic quantity of potassium iodide were refluxed in 10 ml acetonitrile for 8 hours. Then the reaction was stopped and 150 ml dichloromethane were added to the reaction mixture after it had become cold. The resulting solution was washed with 70 ml aqueous 2N sodium hydroxide solution and then twice with water, dried over sodium sulfate, and the solvent was distilled off. The crude title compound which remained as a residue was purified by chromatography on silica gel using ethyl acetate/methanol (8:2) as eluent. 4.8 g N-(4-[2-((1S,2S,5S)-6,6-dimethylbicyclo[3,1,1]hept-2-yl)-ethoxy]butyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylamine were obtained. Rf value=0.2. In addition, it was possible to isolate 2.3 g of unreacted 4-[2-((1S,2S,5S)-6,6-dimethylbicyclo[ 3,1,1]hept-2-yl)ethoxy]-butyl chloride. Rf value=0.6.

Workup

  1. washThe resulting solution was washed with 70 ml aqueous 2N sodium hydroxide solution
  2. dry with materialtwice with water, dried over sodium sulfate
  3. distillationthe solvent was distilled off
  4. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-ee563165a9b448469e31f414cadce27a
Source dataset
uspto-grants-1994_03
Patent number
US05294638

Reaction notes

Loading…