Ethyl bromoacetate → HCID 19004075, compound

HRID 2210811Notes

Reaction equation

HRID 2210811 reaction equation
[CH2:1]1[CH:6]2[C:7]3[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=3[CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:5]2[CH2:4][CH2:3][NH:2]1.Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)([O-])[O-].[Na+].[Na+].CC(C)CC(=O)C>O.[I-].[Na+]>[CH2:1]1[CH:6]2[C:7]3[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=3[CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:5]2[CH2:4][CH2:3][N:2]1[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 115194Desmethylmianserin

Product 1

HCID 19004075HCID 19004075, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 962WaterSolvent

Procedure

0.546 g of 1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine, 0.437 g of ethyl bromoacetate; 0.692 g of sodium carbonate and 0.016 g of sodium iodide were added to 20 ml of 4-methyl-2-pentanone, and the mixture was heated under reflux for 16 hours. At the end of this time, the mixture was diluted with water and then extracted with ethyl acetate. The solvent was then removed by evaporation under reduced pressure. The resulting residue was then subjected to column chromatography through silica gel, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to afford 0.602 g (yield 82%) of the title compound as a pale yellow oil. The hydrochloride of this compound, melting at 187°-190° C., may be prepared by similar means to Those described in Example 17.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 16 hours
  3. extractionextracted with ethyl acetate
  4. customThe solvent was then removed by evaporation under reduced pressure
  5. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-adf5d35e90134ff18e3035849cd4ecfc
Source dataset
uspto-grants-1995_10
Patent number
US05461051

Reaction notes

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