Potassium Iodide → HCID 14675604, compound

HRID 2352349Notes

Reaction equation

HRID 2352349 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C@H:8]([CH2:10][N:11]([CH3:15])[CH2:12][C:13]#[CH:14])[OH:9])[CH:5]=[CH:6][CH:7]=1.Cl[CH2:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(OCC)(=O)C.O>[CH3:15][N:11]([CH2:10][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:1][CH2:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)[CH:3]=1)[OH:9])[CH2:12][C:13]#[CH:14]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 203942-(Chloromethyl)quinolineHCID 13914279HCID 13914279, compound

Product 1

HCID 14675604HCID 14675604, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 8.2 g (0.04 mol) of (R)-3-hydroxy-α-[[methyl-(2-propynyl)amino]methyl]benzene methanol, 7.1 g (0.04 mol) of 2-(chloromethyl)quinoline, 13.5 g (0.04 mol) of cesium carbonate, 0.5 g of potassium iodide, and 500 ml of tetahydrofuran is heated for 10 hours with stirring. The mixture is poured into water and ethyl acetate. The ethyl acetate is separated and washed with dilute aqueous sodium chloride solution. The ethyl acetate is dried over anhydrous magnesium sulfate, filtered and evaporated. The residue is chromatographed on silica gel with methylene chloride/isopropanol as eluent. Fractions 11-17 are combined, the solvent is evaporated and the residue, a viscous oil (2.1 g) is dried in vacuo.

Workup

  1. temperatureis heated for 10 hours
  2. customThe ethyl acetate is separated
  3. washwashed with dilute aqueous sodium chloride solution
  4. dry with materialThe ethyl acetate is dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is chromatographed on silica gel with methylene chloride/isopropanol as eluent
  8. customthe solvent is evaporated
  9. dry with materialthe residue, a viscous oil (2.1 g) is dried in vacuo

Sources & evidence

ORD record
ord-17d8d9f44a404531b541db9bf38cb00c
Source dataset
uspto-grants-1989_10
Patent number
US04876346

Reaction notes

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