2-Bromo-1-[3-(methoxymethyl)-4-(phenylmethoxy)phenyl]ethanone → 4-Hydroxy-3-(methoxymethyl)-alpha-[[[6-[2-(4-methoxyphenyl)ethoxy]hexyl]amino]methyl]benzenemethanol

HRID 1165282Notes

Reaction equation

HRID 1165282 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11]CC2C=CC=CC=2)=[C:7]([CH2:19][O:20][CH3:21])[CH:6]=1)=[O:4].[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][NH:39]CC2C=CC=CC=2)=[CH:26][CH:25]=1>C1COCC1.C(O)C>[OH:11][C:8]1[CH:9]=[CH:10][C:5]([CH:3]([CH2:2][NH:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][O:32][CH2:31][CH2:30][C:27]2[CH:26]=[CH:25][C:24]([O:23][CH3:22])=[CH:29][CH:28]=2)[OH:4])=[CH:6][C:7]=1[CH2:19][O:20][CH3:21]

Participants

5

Reactant 2

HCID 124989662-Bromo-1-[3-(methoxymethyl)-4-(phenylmethoxy)phenyl]ethanoneHCID 13588716N-[6-[2-(4-methoxyphenyl)ethoxy]hexyl]benzenemethanamine

Product 1

HCID 198626844-Hydroxy-3-(methoxymethyl)-alpha-[[[6-[2-(4-methoxyphenyl)ethoxy]hexyl]amino]methyl]benzenemethanolYield 48.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-bromo-1-[3-(methoxymethyl)-4-(phenylmethoxy)phenyl]ethanone (1.38 g), N-[6-[2-(4-methoxyphenyl)ethoxy]hexyl]benzenemethanamine (1.35 g) and DEA (1.02 g) in THF (21 ml) was allowed to stand under nitrogen for 20 h. The mixture was filtered and the filtrate evaporated in vacuo to give an oil, a solution of which in ethanol (35 ml) was hydrogenated over pre-reduced 10% PdO-C (50% aqueous, 500 mg) and 5% PtO-C (400 mg). The mixture was filtered through hyflo and evaporated in vacuo to give an oil. Purification by FCC eluting with System B (900:100:5) gave the title compound as a cream solid (0.82 g) m.p. 97.5°-98.5°.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated in vacuo
  3. customto give an oil
  4. filtrationThe mixture was filtered through hyflo
  5. customevaporated in vacuo
  6. customto give an oil
  7. customPurification by FCC
  8. washeluting with System B (900:100:5)

Sources & evidence

ORD record
ord-9870339be2714748aadb004f3a96ecdb
Source dataset
uspto-grants-1990_03
Patent number
US04908386

Reaction notes

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