Triethylamine → 2-(4-Bromophenyl)-2-hydroxy-N-[2-(4-hydroxy-3-methoxyphenyl)-ethyl]-acetamide

HRID 2112293Notes

Reaction equation

HRID 2112293 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12]C(C)(C)O[C:9]2=[O:15])=[CH:4][CH:3]=1.Cl.[NH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([O:27][CH3:28])[CH:21]=1.C(N(CC)CC)C>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:12])[C:9]([NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([O:27][CH3:28])[CH:21]=2)=[O:15])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 113802305-(4-Bromophenyl)-2,2-dimethyl-1,3-dioxolan-4-oneHCID 119576213-Methoxy-4-hydroxyphenylethylamine hydrochloride

Product 1

HCID 112459552-(4-Bromophenyl)-2-hydroxy-N-[2-(4-hydroxy-3-methoxyphenyl)-ethyl]-acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(4-Bromophenyl)-2,2-dimethyl-1,3-dioxolan-4-one (15 g; 55 mmol) is dissolved in 50 ml of methanol. 4-(2-Aminoethyl)-2-methoxyphenol hydrochloride (14 g; 69 mmol) and triethylamine (7 g; 69 mmol) are added and the mixture is stirred for 72 hours at room temperature. The solvent is removed in vacuum and the residue is extracted with ethyl acetate and the combined organic phases are washed with brine, dried over sodium sulfate and evaporated to dryness. The remaining 2-(4-bromophenyl)-2-hydroxy-N-[2-(4-hydroxy-3-methoxyphenyl)-ethyl]-acetamide is purified by chromatography on silica gel.

Workup

  1. customThe solvent is removed in vacuum
  2. extractionthe residue is extracted with ethyl acetate
  3. washthe combined organic phases are washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customThe remaining 2-(4-bromophenyl)-2-hydroxy-N-[2-(4-hydroxy-3-methoxyphenyl)-ethyl]-acetamide is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c76ee055e05b4c8689b9f7a5f0044351
Source dataset
uspto-grants-2009_04
Patent number
US07521579B2

Reaction notes

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