Hydrochloric Acid → trans-(+/-)-2-Methoxy-6-n-propyl-5,5a,6,7,8,9,9a,10octahydropyrimido[4,5-g]quinoline dihydrochloride

HRID 2164871Notes

Reaction equation

HRID 2164871 reaction equation
[CH2:1]([N:4]1[C@H:13]2[C@@H:8]([CH2:9][C:10](=O)[C:11](=[CH:14]N(C)C)[CH2:12]2)[CH2:7][CH2:6][CH2:5]1)[CH2:2][CH3:3].S(O)(O)(=O)=O.[CH3:24][O:25][C:26](=[NH:28])[NH2:27].C(O)C.[ClH:32]>CO.C(OCC)(=O)C>[ClH:32].[ClH:32].[CH3:24][O:25][C:26]1[N:27]=[CH:14][C:11]2[CH2:12][C@H:13]3[C@@H:8]([CH2:7][CH2:6][CH2:5][N:4]3[CH2:1][CH2:2][CH3:3])[CH2:9][C:10]=2[N:28]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 169039Carbamimidic acid, methyl ester, sulfate (1:1)HCID 54074822trans-(+/-)-1-n-Propyl-6-oxo-7-dimethylaminomethylenedecahydroquinoline

Product 1

HCID 18596521trans-(+/-)-2-Methoxy-6-n-propyl-5,5a,6,7,8,9,9a,10octahydropyrimido[4,5-g]quinoline dihydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Following the procedure of Example 1, a reaction mixture was prepared from trans-(±)-1-n-propyl-6-oxo-7-dimethylaminomethylenedecahydroquinoline and O-methylisourea hydrogen sulfate in 20 ml. of anhydrous ethanol. The reaction mixture was heated to reflux temperature overnight and was then evaporated to dryness. The resulting residue was dissolved in chloroform. The chloroform solution was chromatographed over florisil using chloroform containing increasing amounts (0-15%) of methanol as the eluant. Fraction 5 was shown by tlc to contain trans-(±)-2-methoxy-6-n-propyl-5,5a,6,7,8,9,9a,10-octahydropyrimido[4,5-g]quinoline formed in the above reaction. The solvent was removed in vacuo leaving a residual yellow oil. The yellow oil was dissolved in methanol and the methanolic solution saturated with gaseous hydrogen chloride. Ethyl acetate was added to the hot methanol solution to the point of incipient precipitation. Upon cooling, yellow crystals of trans-(±)-2-methoxy-6-n-propyl-5,5a,6,7,8,9,9a,10octahydropyrimido[4,5-g]quinoline dihydrochloride formed which were collected by filtration. The product had a molecular ion at 261.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux temperature overnight
  3. customwas then evaporated to dryness
  4. dissolutionThe resulting residue was dissolved in chloroform
  5. customThe chloroform solution was chromatographed over florisil
  6. temperatureincreasing amounts (0-15%) of methanol as the eluant
  7. customformed in the above reaction
  8. customThe solvent was removed in vacuo
  9. customleaving a residual yellow oil
  10. temperatureUpon cooling

Sources & evidence

ORD record
ord-6b64764dd0ab4462b3c9a5ed580c44a7
Source dataset
uspto-grants-1985_03
Patent number
US04507478

Reaction notes

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