Dimethylcarbamoyl Chloride → HCID 131718434, compound

HRID 1109102Notes

Reaction equation

HRID 1109102 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][CH2:20][CH2:21][N:22]3[C:26](=[O:27])[C:25]4=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]4[C:23]3=[O:32])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH3:33][N:34]([CH3:38])[C:35]([Cl:37])=[O:36].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[ClH:37].[CH3:33][N:34]([CH3:38])[C:35](=[O:36])[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][CH2:20][CH2:21][N:22]3[C:23](=[O:32])[C:24]4=[CH:31][CH:30]=[CH:29][CH:28]=[C:25]4[C:26]3=[O:27])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 131718430HCID 131718430, compound

Product 1

HCID 131718434HCID 131718434, compoundYield 34.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 0.30 g (0.66 mmol) of rac-cis-N-[6-(1,2,3a,4,5,9b-hexahydro-6-hydroxy-3H-benzo[e]indol-3-yl)-hexyl]phthalimide hydrochloride, 0.06 ml (0.66 mmol) of dimethylcarbamoyl chloride, 0.19 ml (1.32 mmol) of triethylamine and 0.08 g (0.66 mmol) of 4-dimethylaminopyridine in 10 ml of toluene was boiled under reflux for 24 hours and then poured into saturated aqueous sodium hydrogen carbonate solution. The mixture was extracted with methylene chloride, 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 dissolved in methylene chloride. The solution was treated with ethanolic HCl and concentrated. The residue was dissolved in methylene chloride, ether was added thereto and the solvent was distilled off. There was obtained 0.12 g (32%) of rac-cis-2,3,3a,4,5,9b-hexahydro-3-(6-phthalimidohexyl)-1H-benzo[e]indol-6-yl dimethylcarbamate hydrochloride as a foam.

Workup

  1. temperatureunder reflux for 24 hours
  2. extractionThe mixture was extracted with methylene chloride
  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 methylene chloride
  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-5c55c38943da4ee096ac8a3204891e66
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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