Sodium Carbonate → HCID 86748237, compound

HRID 2379444Notes

Reaction equation

HRID 2379444 reaction equation
[CH2:1]1[C@@H: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.Cl[CH2:21][CH2:22][O:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].C(=O)([O-])[O-].[Na+].[Na+]>[I-].[Na+].CC(C)CC(=O)C>[CH2:1]1[C@@H: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][CH2:22][O:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 153934Dibenzo(c,f)pyrazino(1,2-a)azepine, 1,2,3,4,10,14b-hexahydro-, (14bS)-HCID 10964894Ethyl 2-(2-chloroethoxy)acetate

Product 1

HCID 86748237HCID 86748237, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

32.48 g of (S)-1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine (prepared as described in Preparation 3), 22.7 g of ethyl 2-chloroethoxyacetate, 48.9 g of sodium carbonate and 0.79 g of sodium iodide were added to 340 ml of 4-methyl-2-pentanone, and the mixture was heated under reflux for 16 hours. At the end of this time, it was cooled to room temperature and was filtered using a Celite filter aid, and the filtrate was concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography through silica gel eluted with a 1:1 by volume mixture of ethyl acetate and hexane, to give 44.85 g (yield 91%) of the title compound as a pale yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 16 hours
  3. filtrationwas filtered
  4. filtrationfilter aid
  5. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  6. washeluted with a 1:1 by volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-b875e032fc4549799fc97eb4dfef0786
Source dataset
uspto-grants-1994_11
Patent number
US05362725

Reaction notes

Loading…