Nonanoic Acid → N-(4-benzyloxy-3,5-dimethylphenyl)nonaneamide

HRID 728349Notes

Reaction equation

HRID 728349 reaction equation
[CH2:1]([O:8][C:9]1[C:15]([CH3:16])=[CH:14][C:12]([NH2:13])=[CH:11][C:10]=1[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18](O)(=[O:27])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>CCOCC>[CH2:1]([O:8][C:9]1[C:15]([CH3:16])=[CH:14][C:12]([NH:13][C:18](=[O:27])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:11][C:10]=1[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8158Nonanoic AcidHCID 149886364-(Benzyloxy)-3,5-dimethylaniline

Product 1

HCID 14988639N-(4-benzyloxy-3,5-dimethylphenyl)nonaneamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.0 g of 4-benzyloxy-3,5-dimethylaniline and 30 ml of nonanoic acid are stirred at 150° C. for 3 hours. To the reaction mixture is added 100 ml of ether, and the mixture is washed with an aqueous 10 % sodium hydroxide and water, and dried followed by evaporation of the solvent. The residue is purified by silica gel column chromatography [Solvent:chloroform-ethanol (10:1)], and from the eluate is obtained 260 mg of N-(4-benzyloxy-3,5-dimethylphenyl)nonaneamide as an oily product.

Workup

  1. washthe mixture is washed with an aqueous 10 % sodium hydroxide and water
  2. customdried
  3. customfollowed by evaporation of the solvent
  4. customThe residue is purified by silica gel column chromatography [Solvent:chloroform-ethanol (10:1)]

Sources & evidence

ORD record
ord-7e2471cb44834d7c8020895ae6beae6b
Source dataset
uspto-grants-1991_09
Patent number
US05047555

Reaction notes

Loading…