Phenyl Isothiocyanate → HCID 54171942, compound

HRID 1005328Notes

Reaction equation

HRID 1005328 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([OH:9])[CH2:2]2.[C:10]1([N:16]=[C:17]=[S:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(OCC)(=O)C.CCOCC>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([O:9][C:17](=[S:18])[NH:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:2]2

Participants

4

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 15381(+-)-3-Quinuclidinol

Product 1

HCID 54171942HCID 54171942, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 21584169Diethylether ethylacetateSolvent

Procedure

3-Quinuclidinol and phenyl isothiocyanate were used. The reaction solution was heated at reflux under nitrogen for 6 days. The reaction solution was chromatographed using silica gel and elution with 10% methanol in methylene chloride followed by a solution of methylene chloride/methanol/ammonium hydroxide (9:1:0.1) to afford a white foam. This foam was dissolved in ethyl acetate/ether (1:9, 10 mL/g of foam), and the resulting cloudy solution was filtered through diatomaceous earth. The resultant filtrate was evaporated under reduced pressure, and the residual foam was crystallized from ethyl acetate/hexanes (1:3) to afford the title compound (29%) as a white solid: mp 132.0-133.0° C.; FAB LRMS m /z (relative intensity, %) 263 (MH+, 14), 110 (100).

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureat reflux under nitrogen for 6 days
  3. customThe reaction solution was chromatographed
  4. washsilica gel and elution with 10% methanol in methylene chloride
  5. customto afford a white foam
  6. filtrationthe resulting cloudy solution was filtered through diatomaceous earth
  7. customThe resultant filtrate was evaporated under reduced pressure
  8. customthe residual foam was crystallized from ethyl acetate/hexanes (1:3)

Sources & evidence

ORD record
ord-ee181c607f234eb3ac1e50549ae1278b
Source dataset
uspto-grants-2000_04
Patent number
US06054464

Reaction notes

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