Diethylaminoethyl chloride → N-[3,5-bis(decyloxy)phenyl]-N-[2-[2-(diethylamino)ethoxy]-2-oxoethyl]glycine 2-(diethylamino)ethyl ester dihydrochloride

HRID 1110303Notes

Reaction equation

HRID 1110303 reaction equation
[C:1]([CH2:4][N:5]([C:10]1[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:13]=[C:12]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:11]=1)[CH2:6][C:7]([OH:9])=[O:8])([OH:3])=[O:2].[CH2:38]([N:40]([CH2:44][CH3:45])[CH2:41][CH2:42][Cl:43])[CH3:39].[CH:46]([N:49]([CH2:53][CH3:54])[CH:50](C)[CH3:51])(C)[CH3:47]>CN(C=O)C>[ClH:43].[ClH:43].[CH2:38]([N:40]([CH2:44][CH3:45])[CH2:41][CH2:42][O:2][C:1](=[O:3])[CH2:4][N:5]([C:10]1[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:13]=[C:12]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:11]=1)[CH2:6][C:7]([O:9][CH2:47][CH2:46][N:49]([CH2:53][CH3:54])[CH2:50][CH3:51])=[O:8])[CH3:39]

Participants

5

Reactant 3

HCID 13364Diethylaminoethyl chlorideHCID 81531DiisopropylethylamineHCID 192621N-(carboxymethyl)-N-(3,5-bis(decyloxy)-phenyl)glycine

Product 1

HCID 67788036N-[3,5-bis(decyloxy)phenyl]-N-[2-[2-(diethylamino)ethoxy]-2-oxoethyl]glycine 2-(diethylamino)ethyl ester dihydrochlorideYield 36.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.50 g (0.96 mmol) of N-(carboxymethyl)-N-[3,5-bis(decyloxy)phenyl]glycine, 1.3 g (9.6 mmol) of 2-diethylaminoethyl chloride and 1.34 ml (7.7 mmol) of N,N-diisopropyl ethylamine in 15 ml of DMF was stirred at room temperature for 48 hours. The reaction mixture was concentrated on the oil pump and the residue was treated with NaHCO3 solution. The product was extracted with ethyl acetate and the dried extract was concentrated at reduced pressure to an oil which was purified by chromatography on 25 g of 230-400 mesh silica gel using methylene chloride(90):methanol(10);concentrated ammonium hydroxide(0.1). The resultant pure free base (0.51 g) was converted to the dihydrochloride salt by treatment of a methylene chloride solution was 0.95 ml of 3N HCl in ethanol. After concentration, the product was dissolved in ether and stored at -18° until crystals formed. Filtration gave 0.28 g, mp 132°-135° of N-[3,5-bis-(decyloxy)phenyl]-N-[ 2-[2-(diethylamino)ethoxy]-2-oxoethyl]glycine 2-(diethylamino)ethyl ester dihydrochloride.

Workup

  1. concentrationThe reaction mixture was concentrated on the oil pump
  2. additionthe residue was treated with NaHCO3 solution
  3. extractionThe product was extracted with ethyl acetate
  4. extractionthe dried extract
  5. concentrationwas concentrated at reduced pressure to an oil which
  6. customwas purified by chromatography on 25 g of 230-400 mesh silica gel
  7. concentrationAfter concentration
  8. dissolutionthe product was dissolved in ether
  9. customstored at -18° until crystals
  10. customformed
  11. filtrationFiltration

Sources & evidence

ORD record
ord-408791bd17b845508e01bbcc0501ffe4
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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