N,N-Dimethylethylenediamine → N-[2-(dimethylamino)ethyl]-4-[[2-(2-naphthalenyloxy)ethyl]oxy]-alpha-oxobenzeneacetamide

HRID 2225759Notes

Reaction equation

HRID 2225759 reaction equation
C[O:2][C:3](=O)[C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[CH:7][CH:6]=1.[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30][NH2:31]>CO>[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30][NH:31][C:3](=[O:2])[C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 541704664-[2-(2-Naphthalenyloxy)ethoxy]-alpha-oxobenzeneacetic acid methyl ester

Product 1

HCID 19004527N-[2-(dimethylamino)ethyl]-4-[[2-(2-naphthalenyloxy)ethyl]oxy]-alpha-oxobenzeneacetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-[[2-(2-naphthalenyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester (0.5 g) in methanol (75 mL) was treated with N,N-dimethylethylenediamine (0.2 mL) and the mixture was refluxed for 18 hours. The solvents were removed by evaporation and the residue was purified by HPLC (ethyl acetate-methanol-triethylamine; 95:5:2) followed by crystallization from ethyl acetate-hexane to give 0.28 g of N-[2-(dimethylamino)ethyl]-4-[[2-(2-naphthalenyloxy)ethyl]oxy]-alpha-oxobenzeneacetamide as a colorless solid, mp 102°-104° C.

Workup

  1. temperaturethe mixture was refluxed for 18 hours
  2. customThe solvents were removed by evaporation
  3. customthe residue was purified by HPLC (ethyl acetate-methanol-triethylamine; 95:5:2)
  4. customfollowed by crystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a607d3c7e8de431e9fe37538d2f5d57c
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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