Pyridine → 6-((2-Ethylhexyl)(phenyl)amino)hexyl acetate

HRID 607491Notes

Reaction equation

HRID 607491 reaction equation
[CH2:1]([CH:3]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:4][N:5]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH3:2].[C:23](OC(=O)C)(=[O:25])[CH3:24].N1C=CC=CC=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>ClCCl.O>[C:23]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][N:5]([CH2:4][CH:3]([CH2:1][CH3:2])[CH2:19][CH2:20][CH2:21][CH3:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:25])[CH3:24]

Participants

7

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 24436Sodium SulfateHCID 670462816-((2-Ethylhexyl)(phenyl)amino)hexan-1-ol

Product 1

HCID 578577296-((2-Ethylhexyl)(phenyl)amino)hexyl acetateYield 93.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

6-((2-ethylhexyl)(phenyl)amino)hexan-1-ol (8.0 g, 0.023 mol) and dichloromethane (100 ml) were loaded into a three-neck flask, stirred, and added with acetic anhydride (2.8 g, 0.028 mol) and pyridine (3.0 g, 0.038 mol). The mixture was allowed to react at 40° C. for 12 hours with stirring. The reaction product was transferred into a separate funnel, and was then added with water and dichloromethane, after which the organic layer was isolated therefrom, dehydrated using sodium sulfate, and then distilled under reduced pressure. Subsequently, the obtained viscous liquid was separated through silica column chromatography, thus obtaining 7.5 g of a yellowish transparent liquid.

Workup

  1. customto react at 40° C. for 12 hours
  2. stirringwith stirring
  3. customThe reaction product was transferred into a separate funnel
  4. customafter which the organic layer was isolated
  5. distillationdistilled under reduced pressure
  6. customSubsequently, the obtained viscous liquid was separated through silica column chromatography

Sources & evidence

ORD record
ord-f3b9171a85224812a8fd2acec1063b2c
Source dataset
uspto-grants-2011_03
Patent number
US07915428B2

Reaction notes

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