Ethyl Acetate → 3-(1,2,3,4,10,14b-Hexahydrodibenzo[c,f]pyrazino[1,2,a]azepin-2-yl)propyl carbamate

HRID 2260144Notes

Reaction equation

HRID 2260144 reaction equation
ClC(Cl)(Cl)[C:3]([N:5]=C=O)=[O:4].[CH2:10]1[CH:15]2[C:16]3[CH:28]=[CH:27][CH:26]=[CH:25][C:17]=3[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:14]2[CH2:13][CH2:12][N:11]1[CH2:29][CH2:30][CH2:31][OH:32].C(OCC)(=O)C>C(Cl)Cl>[C:3](=[O:4])([O:32][CH2:31][CH2:30][CH2:29][N:11]1[CH2:12][CH2:13][N:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][C:17]3[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=3[CH:15]2[CH2:10]1)[NH2:5]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 76400Trichloroacetyl isocyanateHCID 18999734HCID 18999734, compound

Product 1

HCID 189997193-(1,2,3,4,10,14b-Hexahydrodibenzo[c,f]pyrazino[1,2,a]azepin-2-yl)propyl carbamateYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.2 ml of trichloroacetyl isocyanate were added to a solution of 400 mg of 3-(1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepin-2-yl)propanol (prepared as described in Example 16) in 20 ml of methylene chloride, whilst ice-cooling, and the mixture was stirred at room temperature for 2 hours. At the end of this time, the solvent was removed by distillation under reduced pressure. The resulting residue was dissolved in 22 ml of methanol, 9.0 g of silica gel were added to the solution and the mixture was stirred at room temperature for 15 hours. At the end of this time, the mixture was filtered using a Celite (trade mark) filter aid, and the filtrate was concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through silica gel eluted with ethyl acetate, to give, after recrystallization from ethyl acetate, 260 mg (yield 59%) of the title compound as crystals, melting at 160°-161° C.

Workup

  1. temperaturecooling
  2. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  3. dissolutionThe resulting residue was dissolved in 22 ml of methanol
  4. addition9.0 g of silica gel were added to the solution
  5. stirringthe mixture was stirred at room temperature for 15 hours
  6. filtrationAt the end of this time, the mixture was filtered
  7. filtrationfilter aid
  8. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  9. washeluted with ethyl acetate
  10. customto give

Sources & evidence

ORD record
ord-f617efb7077247568b8ce49ac6765b6b
Source dataset
uspto-grants-1995_12
Patent number
US05476848

Reaction notes

Loading…