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

HRID 1757861
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HRID 1757861 반응식
[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]
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

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 convened to the dihydrochloride salt by treatment of a methylene chloride solution with 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.

후처리

  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

출처 및 근거

ORD 기록
ord-9e79b446b8f2450baafd57c363b90a13
출처 데이터셋
uspto-grants-1995_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05446189

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