Water → rac-cis-2,3,3a,4,5,9b-hexahydro-3-(4-phthalimidobutyl)-1H-benzo[e]indol-6-yl dimethylcarbamate hydrochloride

HRID 1109100Notes

Reaction equation

HRID 1109100 reaction equation
Cl.[OH:2][C:3]1[C:15]2[CH2:14][CH2:13][C@H:12]3[C@H:8]([CH2:9][CH2:10][N:11]3[CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[C:24](=[O:25])[C:23]4=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]4[C:21]3=[O:30])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH3:31][N:32]([CH3:36])[C:33]([Cl:35])=[O:34].C(N(CC)CC)C.O>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[ClH:35].[CH3:31][N:32]([CH3:36])[C:33](=[O:34])[O:2][C:3]1[C:15]2[CH2:14][CH2:13][C@H:12]3[C@H:8]([CH2:9][CH2:10][N:11]3[CH2:16][CH2:17][CH2:18][CH2:19][N:20]3[C:21](=[O:30])[C:22]4=[CH:29][CH:28]=[CH:27][CH:26]=[C:23]4[C:24]3=[O:25])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 131718426rac-N-[4-(cis-1,2,3a, 4,5,9b-hexahydro-6-hydroxy-3H-benzo[e]indol-3-yl)butyl]phthalimide hydrochloride

Product 1

HCID 131718428rac-cis-2,3,3a,4,5,9b-hexahydro-3-(4-phthalimidobutyl)-1H-benzo[e]indol-6-yl dimethylcarbamate hydrochlorideYield 79%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 0.12 g (0.28 mol) of rac-N-[4-(cis-1,2,3a, 4,5,9b-hexahydro-6-hydroxy-3H-benzo[e]indol-3-yl)butyl]phthalimide hydrochloride, 0.03 ml (0.34 mmol) of dimethylcarbamoyl chloride, 0.05 ml (0.34 mmol) of triethylamine and 0.042 g (0.34 mmol) of 4-dimethylaminopyridine in 10 ml of toluene was boiled under reflux for 4 hours and then poured into water. The mixture was extracted with toluene, the extracts were dried with sodium sulphate and the solvent was distilled off in a vacuum. The residue was chromatographed over silica gel with methylene chloride/methanol (20:1) and then dissolved in ethanol. The solution was treated with ethanolic HCl and concentrated. The residue was dissolved in methylene chloride, ether was added thereto, the solvent was distilled off and there was obtained 0.11 g (79%) of rac-cis-2,3,3a,4,5,9b-hexahydro-3-(4-phthalimidobutyl)-1H-benzo[e]indol-6-yl dimethylcarbamate hydrochloride as a foam.

Workup

  1. temperatureunder reflux for 4 hours
  2. extractionThe mixture was extracted with toluene
  3. dry with materialthe extracts were dried with sodium sulphate
  4. distillationthe solvent was distilled off in a vacuum
  5. customThe residue was chromatographed over silica gel with methylene chloride/methanol (20:1)
  6. dissolutiondissolved in ethanol
  7. additionThe solution was treated with ethanolic HCl
  8. concentrationconcentrated
  9. dissolutionThe residue was dissolved in methylene chloride
  10. additionether was added
  11. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-de68985e50f64088b112d7b7903c96fa
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

Loading…