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

HRID 7075

Reaction equation

HRID 7075 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]3[CH2:26][CH2:25][CH:24]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:23][CH2:22]3)[CH:16]=2)=[O:13])=[CH:7][C:6]=1[O:31][CH3:32].[NH2:33][CH2:34][CH2:35][OH:36].C(N(CC)CC)C.C(Cl)(Cl)Cl>C(#N)C>[C:27]([CH:24]1[CH2:25][CH2:26][CH:21]([C:17]2[CH:16]=[C:15]([NH:14][C:12](=[O:13])[CH2:11][C:8]3[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][NH:33][CH2:34][CH2:35][OH:36])=[C:6]([O:31][CH3:32])[CH:7]=3)[CH:20]=[CH:19][CH:18]=2)[CH2:22][CH2:23]1)([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 6212ChloroformHCID 8471TriethylamineHCID 220196274-(2-bromoethoxy)-N-[3-(4-tert-butylcyclohexan-1-yl)phenyl]-3-methoxyphenylacetamide

Product 1

HCID 22019647N-[3-(4-tert-butylcyclohexan-1-yl)phenyl]-4-[2-[N-(2-hydroxyethyl)amino]ethoxy]-3-methoxyphenylacetamideYield 88.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 18 hours
  3. washthe mixture is washed with water
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 20% chloroform/methanol)

Sources & evidence

ORD record
ord-ca4213a13adb45e8b1ae784052865be6
Source dataset
uspto-grants-2006_08
Patent number
US07084176B2

Linked notes

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