Dimethylcarbamoyl Chloride → HCID 131718443, compound

HRID 1109108Notes

Reaction equation

HRID 1109108 reaction equation
Cl.C([N:5]1[C@@H:13]2[C@@H:8]([C:9]3[C:17]([OH:18])=[CH:16][CH:15]=[CH:14][C:10]=3[CH2:11][CH2:12]2)[CH2:7][CH2:6]1)CC.[CH3:19][N:20]([CH3:24])[C:21]([Cl:23])=[O:22].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[ClH:23].[CH3:19][N:20]([CH3:24])[C:21](=[O:22])[O:18][C:17]1[C:9]2[C@@H:8]3[C@H:13]([CH2:12][CH2:11][C:10]=2[CH:14]=[CH:15][CH:16]=1)[NH:5][CH2:6][CH2:7]3

Participants

7

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 131718445HCID 131718445, compound

Product 1

HCID 131718443HCID 131718443, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 1.10 g (0.004 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-3-propyl-1H-benzo[e]indol-9-ol hydrochloride, 0.61 g (0.005 mol) of dimethylcarbamoyl chloride, 1.4 ml (0.01 mol) of triethylamine and 0.61 g (0.005 mol) of 4-dimethylaminopyridine in 40 ml of toluene was boiled under reflux for 4 hours and then poured into a saturated aqueous sodium hydrogen carbonate solution, whereupon the mixture was extracted with methylene chloride. The extract was dried with sodium sulphate, filtered and evaporated in a vacuum. The residue was purified by chromatography over silica gel with methylene chloride/methanol (99:1) and over aluminum oxide with methylene chloride and dissolved in ethanol. After the addition of ethanolic HCl the solvent was distilled off. There were obtained 1.20 g (86%) of rac-cis-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]indol-9-yl dimethylcarbamate hydrochloride as a foam.

Workup

  1. temperatureunder reflux for 4 hours
  2. extractionwas extracted with methylene chloride
  3. dry with materialThe extract was dried with sodium sulphate
  4. filtrationfiltered
  5. customevaporated in a vacuum
  6. customThe residue was purified by chromatography over silica gel with methylene chloride/methanol (99:1) and over aluminum oxide with methylene chloride
  7. dissolutiondissolved in ethanol
  8. additionAfter the addition of ethanolic HCl the solvent
  9. distillationwas distilled off

Sources & evidence

ORD record
ord-d1ada9c41c51448bba3c71239d79e5c2
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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