Hydrochloric Acid → (+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-yl ethylcarbamate hydro-chloride

HRID 1109156Notes

Reaction equation

HRID 1109156 reaction equation
[CH:1]1([CH2:7][CH2:8][N:9]2[C@@H:17]3[C@@H:12]([C:13]4[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[C:14]=4[CH2:15][CH2:16]3)[CH2:11][CH2:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:30]([N:32]=[C:33]=[O:34])[CH3:31].C(=O)([O-])O.[Na+].[ClH:40]>C(#N)C.C(O)C>[ClH:40].[CH2:30]([NH:32][C:33](=[O:34])[O:22][C:18]1[C:14]2[CH2:15][CH2:16][C@H:17]3[C@H:12]([CH2:11][CH2:10][N:9]3[CH2:8][CH2:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[C:13]=2[CH:21]=[CH:20][CH:19]=1)[CH3:31]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 86747896(+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-ol

Product 1

HCID 86747897(+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-yl ethylcarbamate hydro-chlorideYield 51%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

A suspension of 2.00 g (0.0067 mol) of (+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-ol in 100 ml of acetonitrile was treated with 1.9 ml (0.013 mol) of triethylamine and 2.1 ml (0.027 mol) of ethyl isocyanate. The mixture was boiled under reflux for 20 hours and then poured into aqueous sodium hydrogen carbonate solution, whereupon the mixture was extracted with methylene chloride. After drying the organic phase with sodium sulphate and distillation of the solvent the residue was chromatographed over silica gel with methylene chloride/methanol 20:1. The oil obtained was dissolved in ethanol and treated with an equimolar amount of ethanolic HCl. After concentration the residue was dissolved in methylene chloride, treated with active charcoal and sodium sulphate, filtered and the solvent was distilled off in a vacuum. The residue was suspended in ethyl acetate, filtered off and dried in a vacuum. There were obtained 1.39 g (51%) of (+)-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-6-yl ethylcarbamate hydro-chloride with m.p. 133°-136°.

Workup

  1. temperatureunder reflux for 20 hours
  2. extractionwas extracted with methylene chloride
  3. customAfter drying the organic phase
  4. distillationwith sodium sulphate and distillation of the solvent the residue
  5. customwas chromatographed over silica gel with methylene chloride/methanol 20:1
  6. customThe oil obtained
  7. concentrationAfter concentration the residue
  8. dissolutionwas dissolved in methylene chloride
  9. additiontreated with active charcoal and sodium sulphate
  10. filtrationfiltered
  11. distillationthe solvent was distilled off in a vacuum
  12. filtrationfiltered off
  13. customdried in a vacuum

Sources & evidence

ORD record
ord-5340a90807094cc09ac03cf1ffcd1f43
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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