1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-[2-(Oleoylamino)phenyl]-3-[N-(2,2,5,5-tetramethyl-1,3-dioxane-4-carbonyl)amino]propanamide

HRID 892890Notes

Reaction equation

HRID 892890 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[C:13]([NH:32][C:33]1[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=1[NH2:35])(=[O:31])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].[CH3:40][C:41]1([CH3:57])[O:46][CH:45]([C:47]([NH:49][CH2:50][CH2:51][C:52](O)=[O:53])=[O:48])[C:44]([CH3:56])([CH3:55])[CH2:43][O:42]1>C(Cl)Cl>[C:13]([NH:32][C:33]1[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=1[NH:35][C:52](=[O:53])[CH2:51][CH2:50][NH:49][C:47]([CH:45]1[C:44]([CH3:55])([CH3:56])[CH2:43][O:42][C:41]([CH3:57])([CH3:40])[O:46]1)=[O:48])(=[O:31])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 189385173-[N-(2,2,5,5-Tetramethyl-1,3-dioxane-4-carbonyl)amino]propionic acidHCID 42604663o-Oleoylaminoaniline

Product 1

HCID 67796153N-[2-(Oleoylamino)phenyl]-3-[N-(2,2,5,5-tetramethyl-1,3-dioxane-4-carbonyl)amino]propanamideYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (211 mg) was added to a solution of 372 mg of 2-oleoylaminoaniline and 259 mg of 3-[N-(2,2,5,5-tetramethyl-1,3-dioxane-4-carbonyl)amino]propionic acid in 30 ml of methylene chloride under ice cooling. The mixture was stirred in situ for one night. The reaction mixture was washed with water and dried over anhydrous sodium sulfate, filtered and the filtate evaporation under vacuum to obtain the crude title products. Then, the residue obtained was subjected to silica gel column chromatography to obtain 500 mg of the title compound (yield: 82%).

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customthe filtate evaporation under vacuum
  5. customto obtain the crude title products
  6. customThen, the residue obtained

Sources & evidence

ORD record
ord-79dd72c185834bb6be6210b6151eb400
Source dataset
uspto-grants-1992_06
Patent number
US05120738

Reaction notes

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