Pyridine → N-(3-Hydroxypropyl)oleamide

HRID 1162423Notes

Reaction equation

HRID 1162423 reaction equation
N[CH:2]([OH:5])[CH2:3][CH3:4].[N:6]1C=CC=CC=1.[C:12](Cl)(=[O:30])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>C(Cl)Cl.C(Cl)(Cl)Cl>[OH:5][CH2:2][CH2:3][CH2:4][NH:6][C:12](=[O:30])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 3

HCID 1049PyridineHCID 52566581-aminopropanolHCID 5364783Oleoyl chloride

Product 1

HCID 13932031N-(3-Hydroxypropyl)oleamide

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-aminopropanol (4.04 ml, 52.8 mmol) and pyridine (4.27 ml, 52.8 mmol) in methylene chloride was slowly added oleoyl chloride (5 ml, 15.1 mmol). After 2 hours, the mixture was diluted with chloroform and washed with ammonium chloride (3×), brine (3×) and dried over sodium sulfate. Column chromatography (15% acetone/chloroform to 50% acetone/chloroform) provided the product as white solid.

Workup

  1. washwashed with ammonium chloride (3×), brine (3×)
  2. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-baf2f9ed23d040e3b34b79139cb03665
Source dataset
uspto-grants-2010_10
Patent number
US07820703B2

Reaction notes

Loading…