Potassium Carbonate → (+/-) trans-4,5,5a,6,7,8,9,9a-Octahydro-6-propyloxazolo[4,5-f]quinolin-2-amine

HRID 34660Notes

Reaction equation

HRID 34660 reaction equation
[N:1]1[C:5]2[C@H:6]3[C@H:11]([CH2:12][CH2:13][C:4]=2[O:3][C:2]=1[NH2:14])[NH:10][CH2:9][CH2:8][CH2:7]3.C(=O)([O-])[O-].[K+].[K+].I[CH2:22][CH2:23][CH3:24]>C(#N)C>[CH2:22]([N:10]1[C@@H:11]2[C@H:6]([C:5]3[N:1]=[C:2]([NH2:14])[O:3][C:4]=3[CH2:13][CH2:12]2)[CH2:7][CH2:8][CH2:9]1)[CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 70416489(+/-) trans-4,5,5a,6,7,8,9,9a-Octahydrooxazolo[4,5-f]quinolin-2-amine

Product 1

HCID 70416172(+/-) trans-4,5,5a,6,7,8,9,9a-Octahydro-6-propyloxazolo[4,5-f]quinolin-2-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (±) trans-4,5,5a,6,7,8,9,9a-octahydrooxazolo[4,5-f]quinolin-2-amine, 1.46 g (5.0 mmol), 3.6 g (26 mmol) of finely ground potassium carbonate and 2.5 ml (25.6 mmol) of 1-iodopropane in 250 ml of acetonitrile is refluxed, under nitrogen, for 24 hours. The mixture is cooled, filtered through a pad of Celite, concentrated and partitioned between brine and chloroform. The organic extract is dried and concentrated. Chromatography of the mixture on silica gel gives (±) trans-4,5,5a,6,7,8,9,9a-octahydro-6-propyloxazolo[4,5-f]quinolin-2-amine. The procedure just described can be applied to (±) trans-4,5,5a,6,7,8,9,9a-octahydrooxazolo[5,4-f]quinolin-2-amine to give (±) trans-4,5,5a,6,7,8,9,9a-octahydro-6-propyloxazolo [5,4-f]quinolin-2-amine.

Workup

  1. temperatureis refluxed, under nitrogen, for 24 hours
  2. temperatureThe mixture is cooled
  3. filtrationfiltered through a pad of Celite
  4. concentrationconcentrated
  5. custompartitioned between brine and chloroform
  6. extractionThe organic extract
  7. customis dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f0952a302a9c47dc962e9fb89cee16cd
Source dataset
uspto-grants-1988_08
Patent number
US04762843

Reaction notes

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