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

HRID 1841642Notes

Reaction equation

HRID 1841642 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>C(O)C>[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 702EthanolSolvent

Procedure

5-(4-Bromo-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-one (15 g, 55 mmol) is dissolved in 50 ml of ethanol. 4-(2-Amino-ethyl)-2-methoxy-phenol hydrochloride (14 g, 69 mmol) and triethylamine (7.0 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 1N hydrochloric acid. The aqueous layer is extracted twice with ethyl acetate and the combined organic phases are washed with brine, dried over sodium sulfate and evaporated. The remaining 2-(4-bromo-phenyl)-2-hydroxy-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-acetamide is purified by chromatography on silica gel. 1H-NMR (300 MHz, CDCl3): 2.71 (t, 2H, CH2CH2), 3.54 (t, 2H, CH2CH2), 3.80 (s, 3H, OCH3), 5.59 (s, 1H, CHOH), 6.16 (bs, 1H, NH), 6.52-7.35 (m, 7H, CH arom.).

Workup

  1. customThe solvent is removed in vacuum
  2. extractionthe residue is extracted with ethyl acetate and 1N hydrochloric acid
  3. extractionThe aqueous layer is extracted twice with ethyl acetate
  4. washthe combined organic phases are washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe remaining 2-(4-bromo-phenyl)-2-hydroxy-N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-acetamide is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a7877f28317a4f99a5bdbc29e0983f3b
Source dataset
uspto-grants-2004_01
Patent number
US06683211B1

Reaction notes

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