Hydrochloric Acid → HCID 20366864, compound

HRID 616899Notes

Reaction equation

HRID 616899 reaction equation
Cl.Cl.[NH2:3][CH:4]1[CH2:13][CH:12]2[N:7]([CH2:8][CH2:9][C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=32)[CH2:6][CH2:5]1.C(N(CC)CC)C.[CH2:25]([S:27]([Cl:30])(=[O:29])=[O:28])[CH3:26].Cl>ClCCl.C(O)C.CO>[ClH:30].[CH2:25]([S:27]([NH:3][CH:4]1[CH2:13][CH:12]2[N:7]([CH2:8][CH2:9][C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=32)[CH2:6][CH2:5]1)(=[O:29])=[O:28])[CH3:26]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 20366867HCID 20366867, compound

Product 1

HCID 20366864HCID 20366864, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 887MethanolSolventHCID 6344DichloromethaneSolvent3×

Procedure

2-Amino-1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine dihydrochloride (3.65g) was dissolved in dichloromethane (30 ml), and the solution ice-cooled and stirred whilst a solution of triethylamine (2.83 g) in dichloromethane (10 ml) was added. The ice-cooling and stirring were maintained whilst a solution of ethanesulphonyl chloride (2.20 g) in dichloromethane (10 ml) was added dropwise. The reaction was stirred at room temperature for a further 3 hours before washing the solution twice with aliquots of water (50 ml). The dichloromethane solution was evaporated to yield a yellow oil, which was dissolved in ethanol (10 ml) and ethanol saturated with hydrogen chloride was added dropwise until the solution was acidic (pH2). On standing for 0.1 hour white crystals were produced, which, after standing for a further 0.1 hour were removed by filtration to constitute a first crop. After allowing the filtrate to stand for 1 hour the solution was filtered again to produce a second crop of white crystals. A third crop was obtained by evaporation of the filtrate. Thin-layer-chromatography indicated that two products had been formed. The two products were isolated by fractional crystallisation of the three crops from hot methanol to give chromatographically pure 2-ethanesulphonamido-1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine hydrochloride, isomer A (1.13g) and chromatographically pure 2-ethanesulphonamido-1,3,4,6,7,11b-hexahydro-2H-benzo[a]-quinolizine hydrochloride, isomer B (1.05 g). The isomer A hydrochloride had m.p. 234°-6° C (C15H22N2O2S.HCl requires C, 54.45; H, 7.01; N, 8.47%. Found: C, 54.25; H, 6.97; N, 8.18%) and isomer B hydrochloride had m.p. 227°-8° C (C15H22N2O2S.HCl requires C, 54.45; H, 7.01; N, 8.47%. Found: C, 54.46; H, 7.09; N, 8.16%).

Workup

  1. temperaturethe solution ice-cooled
  2. additionwas added
  3. additionwas added dropwise
  4. stirringThe reaction was stirred at room temperature for a further 3 hours
  5. washbefore washing the solution twice with aliquots of water (50 ml)
  6. customThe dichloromethane solution was evaporated
  7. customto yield a yellow oil, which
  8. customwhite crystals were produced
  9. waitwhich, after standing for a further 0.1 hour
  10. customwere removed by filtration
  11. waitto stand for 1 hour
  12. filtrationthe solution was filtered again
  13. customto produce a second crop of white crystals
  14. customA third crop was obtained by evaporation of the filtrate
  15. customhad been formed

Sources & evidence

ORD record
ord-e8c2b31b7b1f4696b3dfc0efaac8755d
Source dataset
uspto-grants-1978_02
Patent number
US04076820

Reaction notes

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