1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(2,6-diisopropylphenyl)-15-hydroxypentadecanamide

HRID 2416949Notes

Reaction equation

HRID 2416949 reaction equation
CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[OH:22][CH2:23][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][C:37]([OH:39])=O.[CH:40]([C:43]1[CH:49]=[CH:48][CH:47]=[C:46]([CH:50]([CH3:52])[CH3:51])[C:44]=1[NH2:45])([CH3:42])[CH3:41]>O.CN(C=O)C>[CH:50]([C:46]1[CH:47]=[CH:48][CH:49]=[C:43]([CH:40]([CH3:42])[CH3:41])[C:44]=1[NH:45][C:37](=[O:39])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][OH:22])([CH3:52])[CH3:51]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 32484DiisopropylanilineHCID 757711-HydroxybenzotriazoleHCID 7836015-Hydroxypentadecanoic acid

Product 1

HCID 22633587N-(2,6-diisopropylphenyl)-15-hydroxypentadecanamideYield 23%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

WSC (4.2 g, 22 mmols) and HOBt (3.0 g, 22 mmols) were added to a DMF (40 ml) solution of the resulting carboxylic acid 15.2 g, 20 mmols) and 2,6-diisopropylaniline (5.3 g, 30 mmols), and stirred at room temperature for 12 hours. Water was added to the reaction mixture, and the precipitate formed was taken out through filtration, and extracted with chloroform. The organic layer was washed with 1 N HCl and saturated saline in that order, and dried with anhydrous sodium sulfate, and the solvent was evaporated. The residue was extracted with ether and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified through silica gel column chromatography (developer:hexane/acetone=5/1) to obtain 1.9 g (yield: 23%) of N-(2,6-diisopropylphenyl)-15-hydroxypentadecanamide.

Workup

  1. customthe precipitate formed
  2. filtrationwas taken out through filtration
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with 1 N HCl and saturated saline in that order
  5. dry with materialdried with anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. extractionThe residue was extracted with ether
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue was purified through silica gel column chromatography (developer:hexane/acetone=5/1)

Sources & evidence

ORD record
ord-8358a298403f4f0082e6a13841486733
Source dataset
uspto-grants-2004_11
Patent number
US06825223B2

Reaction notes

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