Reaction #62932

Reaction equation

(±) trans-(5,6,6a,7,8,9,10,10a-octahydropyrido[2,3-h]quinazolin-2-yl)-carbamic acid, phenylmethyl ester

(±) trans-(5,6,6a,7,8,9,10,10a-Octahydropyrido[2,3-h]quinazolin-2-yl)-carbamic acid, phenylmethyl ester

potassium carbonate

1-iodopropane

→

ammonium hydroxide

title compound

Yield 144.2%

(±) trans-(5,6,6a,7,8,9,10,10a-Octahydro-7-propylpyrido[2,3-h]quinazolin-2-yl)-carbamic acid, phenylmethyl ester

Yield 144.2%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperatureis refluxed, under nitrogen, for 24 hours
2. 2
   TemperatureThe suspension is cooled
3. 3
   Filtrationfiltered through a pad of Celite
4. 4
   Concentrationconcentrated
5. 5
   Otherpartitioned between brine and chloroform
6. 6
   ExtractionThe chloroform extract
7. 7
   Otheris separated
8. 8
   Dryingdried over magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Concentrationconcentrated to a viscous brown oil

Procedure

A mixture of 1.74 g (5.14 mmol) of (±) trans-(5,6,6a,7,8,9,10,10a-octahydropyrido[2,3-h]quinazolin-2-yl)-carbamic acid, phenylmethyl ester, (Example 20), 3.6 g (26.05 mmol) of finely ground potassium carbonate and 2.5 ml (25.63 mmol) of 1-iodopropane in 250 ml acetonitrile is refluxed, under nitrogen, for 24 hours. The suspension is cooled, filtered through a pad of Celite, concentrated and partitioned between brine and chloroform. The chloroform extract is separated, dried over magnesium sulfate, filtered and concentrated to a viscous brown oil. Medium pressure chromatography (silica gel, 2% ammonium hydroxide-98% ethyl acetate) afforded 1.41 g (72%) of the title compound as a white solid; mp 174°-177° C.

Source