2-Bromo-1-[3-(methoxymethyl)-4-(phenylmethoxy)phenyl]ethanone → alpha-[[[5-[2-(4-Fluorophenyl)ethoxy]pentyl]amino]methyl]-4-hydroxy-3-(methoxy methyl)benzenemethanol

HRID 1165281Notes

Reaction equation

HRID 1165281 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].[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:37]CC2C=CC=CC=2)=[CH:25][CH:24]=1>C1COCC1>[F:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:29][CH2:30][O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][NH:37][CH2:2][CH:3]([C:5]2[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH2:19][O:20][CH3:21])[CH:6]=2)[OH:4])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 124989662-Bromo-1-[3-(methoxymethyl)-4-(phenylmethoxy)phenyl]ethanoneHCID 13592787N-[5-(2-(4-fluorophenyl)ethoxy]pentyl]benzenemethanamine

Product 1

HCID 19862695alpha-[[[5-[2-(4-Fluorophenyl)ethoxy]pentyl]amino]methyl]-4-hydroxy-3-(methoxy methyl)benzenemethanolYield 49.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-bromo-1-[3-(methoxymethyl)-4-(phenylmethoxy)phenyl]ethanone (1.0 g), N-[5-(2-(4-fluorophenyl)ethoxy]pentyl]benzenemethanamine (0.91 g), and DEA (0.77 g) in THF (15 ml) was left at room temperature for 18 h, filtered and evaporated. The residue was hydrogenated over 10% Pd-C (0.5 g) and 5% Pt-C (0.5 g), filtered and evaporated. The resulting oil was purified by FCC eluting with System C (80:20:1) to give the title compound as a white solid (0.58 g) m.p. 86°-87°, t.l.c. (System C 80:20:1) Rf 0.25.

Workup

  1. filtrationfiltered
  2. customevaporated
  3. filtrationfiltered
  4. customevaporated
  5. customThe resulting oil was purified by FCC
  6. washeluting with System C (80:20:1)

Sources & evidence

ORD record
ord-b21039e491e347eda39a21d55ce72297
Source dataset
uspto-grants-1990_03
Patent number
US04908386

Reaction notes

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