N,N-Dimethylethylenediamine → HCID 19897069, compound

HRID 1196997Notes

Reaction equation

HRID 1196997 reaction equation
O=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:3]1=2.[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH2:26].C(=O)(O)[O-].[Na+]>C1C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][N:26]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:3]1=2

Participants

6

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 516892Sodium BicarbonateHCID 10333952Methyl (11-oxo-6,11-dihydrodibenzo[b,e]oxepin-2-yl)acetate

Product 1

HCID 19897069HCID 19897069, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 241BenzeneSolvent2×

Procedure

In this example, 22.0 g of methyl 11-oxo-6,11-dihydrodibenz[b,e]oxepin-2-acetate and 68.7 g of N,N-dimethylethylenediamine are dissolved in 700 ml of dried benzene. To the solution is dropwise added a solution of 17.2 ml of titanium tetrachloride in 40 ml of dried benzene and the mixture is stirred at room temperature overnight. A saturated aqueous sodium bicarbonate solution is added thereto. After removing an insoluble solid by filtration, the filtrate is extracted with 500 ml of ethylacetate, washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution in order, and dried over anhydrous sodium sulfate. The solvent is distilled away under reduced pressure and the residue is purified by column chromatography on silica gel with ethylacetate/triethylamine (10/1) as an eluent to obtain 13.8 g of the desired product as a colorless oily matter.

Workup

  1. customAfter removing an insoluble solid
  2. filtrationby filtration
  3. extractionthe filtrate is extracted with 500 ml of ethylacetate
  4. washwashed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution in order
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent is distilled away under reduced pressure
  7. customthe residue is purified by column chromatography on silica gel with ethylacetate/triethylamine (10/1) as an eluent

Sources & evidence

ORD record
ord-a78aa435906b4419a8ef070c9c01781d
Source dataset
uspto-grants-1992_05
Patent number
US05116863

Reaction notes

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