N,N-Dimethyl-1,3-propanediamine → HCID 21832978, compound
Reaction equation
C(N(CC)CC)C.C1(P(Cl)(C2C=CC=CC=2)=O)C=CC=CC=1.[C:23]([NH:42][C:43]1[CH:51]=[CH:50][CH:49]=[CH:48][C:44]=1[C:45]([OH:47])=O)(=[O:41])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40].[CH3:52][N:53]([CH3:58])[CH2:54][CH2:55][CH2:56][NH2:57]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:52][N:53]([CH3:58])[CH2:54][CH2:55][CH2:56][NH:57][C:45]([C:44]1[CH:48]=[CH:49][CH:50]=[CH:51][C:43]=1[NH:42][C:23](=[O:41])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[O:47]Participants
Conditions
- Temperature
- 0 °C
Procedure
Triethylamine (0.44 ml) and diphenylphosphinic chloride (0.48 ml) were added to a suspension of 2-(octadecanoylamino)benzoic acid (0.85 g) in methylene chloride (10 ml). After being stirred for 3 hours at 0° C., the mixture, with N,N-dimethyl-1,3-propanediamine (0.33 ml) added thereto, was stirred for 44 hours at room temperature. The reaction mixture was then diluted with chloroform, washed with saturated sodium hydrogencarbonate aqueous solution and water successively, dried over sodium sulfate anhydride, and concentrated. The residue was purified by silica gel column chromatography (silica gel 20 g, chloroform-methanol), thereby yielding 0.53 g of N-{2-{N-{3-(dimethylamino)propyl}carbamoyl}phenyl}octadecaneamide and 0.37 g of the aimed compound as colorless crystals.
Workup
- stirringwas stirred for 44 hours at room temperature
- washwashed with saturated sodium hydrogencarbonate aqueous solution and water successively
- dry with materialdried over sodium sulfate anhydride
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography (silica gel 20 g, chloroform-methanol)
Sources & evidence
- ORD record
- ord-f54d93357bd446d18fa096f5366d1be9
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05972929
Reaction notes
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