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

HRID 34654Notes

Reaction equation

HRID 34654 reaction equation
[N:1]1[C:10]2[C@@H:9]3[CH2:11][CH2:12][CH2:13][NH:14][C@H:8]3[CH2:7][CH2:6][C:5]=2[CH:4]=[N:3][C:2]=1[NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:33][CH2:34][CH3:35]>C(#N)C>[OH-:17].[NH4+:1].[CH2:33]([N:14]1[C@H:8]2[CH2:7][CH2:6][C:5]3[CH:4]=[N:3][C:2]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[N:1][C:10]=3[C@@H:9]2[CH2:11][CH2:12][CH2:13]1)[CH2:34][CH3:35]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 14233853(+/-) trans-(5,6,6a,7,8,9,10,10a-Octahydropyrido[2,3-h]quinazolin-2-yl)-carbamic acid, phenylmethyl ester

Product 2

HCID 14923Ammonium HydroxideHCID 14233855(+/-) trans-(5,6,6a,7,8,9,10,10a-Octahydro-7-propylpyrido[2,3-h]quinazolin-2-yl)-carbamic acid, phenylmethyl esterYield 144.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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.

Workup

  1. temperatureis refluxed, under nitrogen, for 24 hours
  2. temperatureThe suspension is cooled
  3. filtrationfiltered through a pad of Celite
  4. concentrationconcentrated
  5. custompartitioned between brine and chloroform
  6. extractionThe chloroform extract
  7. customis separated
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to a viscous brown oil

Sources & evidence

ORD record
ord-c0673a36ea004128ba9aff88e2e2c5b8
Source dataset
uspto-grants-1988_08
Patent number
US04762843

Reaction notes

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