Potassium Iodide → HCID 18651839, compound

HRID 248847Notes

Reaction equation

HRID 248847 reaction equation
[CH3:1][C:2]1([CH3:18])[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][CH2:16]Cl.[CH3:19][CH:20]([CH3:27])[CH2:21][O:22][CH2:23][CH2:24][NH:25][CH3:26].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[CH3:1][C:2]1([CH3:18])[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][CH2:16][N:25]([CH2:24][CH2:23][O:22][CH2:21][CH:20]([CH3:27])[CH3:19])[CH3:26]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 19762349HCID 19762349, compoundHCID 57308375HCID 57308375, compound

Product 1

HCID 18651839HCID 18651839, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

15 g of 5-[2-((1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl)ethoxy]pentyl chloride were dissolved in 100 ml of dimethylformamide. 5.13 g of N-[2-(2,2-dimethylethoxy)ethyl]-N-methylamine (Example 12 B)), 12 g of potassium carbonate and 1 g of potassium iodide were added to the solution. The reaction mixture was stirred at a temperature of 80° C. for 12 hours. The reaction mixture was worked up by concentrating it under reduced pressure, adding 100 ml of water to the residue, and extracting the mixture three times with 80 ml portions of dichloromethane. The combined dichloromethane extracts were dried over sodium sulfate, filtered and concentrated. The crude product remaining as a residue was purified by chromatography on silica gel using dichloromethane/methanol as the eluent. 4.1 g of oily N-(5-[2-((1S,2S,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-yl)ethoxy]pent yl)-N-[2-(2,2-dimethylethoxy)ethyl]-N-methylamine were obtained.

Workup

  1. concentrationby concentrating it under reduced pressure
  2. additionadding 100 ml of water to the residue
  3. extractionextracting the mixture three times with 80 ml portions of dichloromethane
  4. dry with materialThe combined dichloromethane extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d1ed64f3fa1c4579ad56f71a06bc1104
Source dataset
uspto-grants-1993_05
Patent number
US05212173

Reaction notes

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