Reaction #7171

Reaction equation

chloroform

Intermediate 5

4-(2-bromoethoxy)-N-[3-(4-tert-butylcyclohexan-1-yl)phenyl]-3-methoxyphenylacetamide

2-aminoethanol

triethylamine

→

desired compound

Yield 88.5%

N-[3-(4-tert-butylcyclohexan-1-yl)phenyl]-4-[2-[N-(2-hydroxyethyl)amino]ethoxy]-3-methoxyphenylacetamide

Yield 88.5%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperaturethe mixture is heated
2. 2
   Temperatureunder reflux for 18 hours
3. 3
   Washthe mixture is washed with water
4. 4
   DryingThe organic layer is dried over sodium sulfate
5. 5
   Otherthe solvent is evaporated under reduced pressure
6. 6
   OtherThe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 20% chloroform/methanol)

Procedure

Intermediate 5 (200 mg), 2-aminoethanol (122 mg) and triethylamine (45 mg) are dissolved in acetonitrile (5 ml), and the mixture is heated under reflux for 18 hours. To the reaction solution is added chloroform, and the mixture is washed with water. The organic layer is dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: gradient from 0% to 20% chloroform/methanol) to give the desired compound (170 mg).

Source