Pyrrolidine → HCID 67935534, compound

HRID 485675Notes

Reaction equation

HRID 485675 reaction equation
Br[C:2]1[S:3][C:4]2[CH2:13][C@H:12]3[C@@H:7]([CH2:8][CH2:9][CH2:10][N:11]3[CH2:14][CH2:15][CH3:16])[CH2:6][C:5]=2[N:17]=1.[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]\[C:26]([OH:28])=[O:27]>CCOCC>[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]\[C:26]([OH:28])=[O:27].[N:18]1([C:2]2[S:3][C:4]3[CH2:13][C@H:12]4[C@@H:7]([CH2:8][CH2:9][CH2:10][N:11]4[CH2:14][CH2:15][CH3:16])[CH2:6][C:5]=3[N:17]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 444266Maleic AcidHCID 18599025HCID 18599025, compound

Product 1

HCID 67935534HCID 67935534, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A reaction mixture, prepared from 6.6 g. of trans-(±)-2-bromo-5-n-propyl-4,4a,5,6,7,8,8a,9-octahydrothiazolo[4,5-g]quinoline and 20 ml. of pyrrolidine, was heated to reflux temperature for about 18 hours and was then cooled. The volatile constituents were removed in vacuo and the resulting residue diluted with water. The aqueous mixture was made strongly basic with concentrated aqueous ammonium hydroxide. The alkaline layer was extracted several times with equal volumes of chloroform. The chloroform extracts were combined, and the combined extracts washed with water and with saturated aqueous sodium chloride and were then dried. The solvent was evaporated therefrom in vacuo. TLC (9:1 CHCl3 /MeOH+a trace of aqueous ammonium hydroxide) showed one spot, more polar than starting material. The residue was therefore dissolved in chloroform and the chloroform solution chromatographed over a florisil column using chloroform as the eluant. Seventeen hundredths grams of a light yellow glass were obtained by this procedure. The glass was dissolved in ether and 0.06 g. of maleic acid in ethereal solution added thereto. A solid maleate salt precipitated. The ether was removed by decantation and the solid salt recrystallized from a mixture of ethanol and ether. Five hundredths grams of trans-(±)-2-(1-pyrrolidinyl)-5-n-propyl-4,4a,5,6,7,8,8a,9-octahydrothiazolo[4,5-g]quinoline maleate were obtained melting with decomposition at 184° C.

Workup

  1. customA reaction mixture, prepared from 6.6 g
  2. temperatureto reflux temperature for about 18 hours
  3. temperaturewas then cooled
  4. customThe volatile constituents were removed in vacuo
  5. additionthe resulting residue diluted with water
  6. extractionThe alkaline layer was extracted several times with equal volumes of chloroform
  7. washthe combined extracts washed with water and with saturated aqueous sodium chloride
  8. customwere then dried
  9. customThe solvent was evaporated
  10. dissolutionThe residue was therefore dissolved in chloroform
  11. customthe chloroform solution chromatographed over a florisil column
  12. customSeventeen hundredths grams of a light yellow glass were obtained by this procedure
  13. customA solid maleate salt precipitated
  14. customThe ether was removed by decantation
  15. customthe solid salt recrystallized from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-dc41dcf7971e435598a0395cac6f01d8
Source dataset
uspto-grants-1985_08
Patent number
US04537893

Reaction notes

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