N,N-Dimethylethylenediamine → HCID 18929471, compound

HRID 1417789Notes

Reaction equation

HRID 1417789 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[C:8]([CH:13]=1)[C:9]([O:11]C)=O)(=[O:3])[CH3:2].[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][NH2:25]>>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[C:8]([CH:13]=1)[C:9]([NH:25][CH2:24][CH2:23][N:22]([CH3:26])[CH3:21])=[O:11])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 86752386HCID 86752386, compound

Product 1

HCID 18929471HCID 18929471, compoundYield 15%

Procedure

A sample of 0.140 g (0.50 mmol) of 5-acetyl-2-(3-carboxypropoxy)-benzoic acid, methyl ester (Example 19) is heated on a steam bath, under dry conditions with 5.49 mL (50.0 mmol) of N,N-dimethylethylenediamine for 5 hours. The mixture is allowed to cool for 20 hours to ambient temperature and evaporated under vacuum at 55° C. The brown gum produced is triturated with ether, and the remaining residue taken up in water and acidified with hydrochloric acid. This is then extracted with ethyl acetate, and the aqueous solution is evaporated under vacuum, leaving a gum. It is next triturated with hot chloroform and this solution is evaporated to give a brown glass. This is chromatographed on a preparatory silica gel plate which is eluted with a 9/1 mixture of chloroform to methanol. The product band is cut from the plate, triturated with the above solvent mixture, filtered, and evaporated leaving 0.025 g (15%) of 5-acetyl-2-(3-carboxypropoxy)-N-(2-dimethylaminoethyl)-benzamide as a light brown gum: MS (FAB) m/e 337.1753 Δ=+0.9 mmμ (M+ +H), 359 (M+ +Na). 1HNMR (CDCl3) is consistent with the desired product.

Workup

  1. temperatureto cool for 20 hours to ambient temperature
  2. customevaporated under vacuum at 55° C
  3. customThe brown gum produced
  4. customis triturated with ether
  5. extractionThis is then extracted with ethyl acetate
  6. customthe aqueous solution is evaporated under vacuum
  7. customleaving a gum
  8. customIt is next triturated with hot chloroform
  9. customthis solution is evaporated
  10. customto give a brown glass
  11. customThis is chromatographed on a preparatory silica gel plate which
  12. washis eluted with a 9/1 mixture of chloroform to methanol
  13. customtriturated with the above solvent mixture
  14. filtrationfiltered
  15. customevaporated

Sources & evidence

ORD record
ord-e8075a89e4314dd49eb618e024de7752
Source dataset
uspto-grants-1999_03
Patent number
US05877296

Reaction notes

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