2-Bromo-1-(4-hydroxy-3-(hydroxymethyl)phenyl)ethan-1-one → 1-[4-Hydroxy-3-(hydroxymethyl)phenyl]-2-[(phenylmethyl)[6-[[6-(2-pyridinyl)hexyl]oxy]hexyl]amino]ethanone

HRID 1088711Notes

Reaction equation

HRID 1088711 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH2:12][OH:13])[CH:6]=1)=[O:4].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][NH:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C1COCC1>[OH:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][N:33]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][O:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=2)=[CH:6][C:7]=1[CH2:12][OH:13]

Participants

4

Reactant 2

HCID 113340552-Bromo-1-(4-hydroxy-3-(hydroxymethyl)phenyl)ethan-1-oneHCID 22161746N-[6-[[6-(2-Pyridinyl)hexyl]oxy]hexyl]benzenemethanamine

Product 1

HCID 221617441-[4-Hydroxy-3-(hydroxymethyl)phenyl]-2-[(phenylmethyl)[6-[[6-(2-pyridinyl)hexyl]oxy]hexyl]amino]ethanoneYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-bromo-1-[4-hydroxy-3-(hydroxymethyl)phenyl]ethanone (1.00 g), N-[6-[[6-(2-pyridinyl)hexy]oxy]hexyl]benzenemethanamine (1.5 g) and DEA (1.58 g) in THF (20 ml) was left to stand for 24 h. The reaction mixture was filtered and the filtrate was concentrated to give an oil which was purified by FCC eluting with System B (95:5:1), to give the title compound as a yellow oil (1.96 g), t.l.c. (System A 80:20:2)) Rf 0.33.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customto give an oil which
  4. customwas purified by FCC
  5. washeluting with System B (95:5:1)

Sources & evidence

ORD record
ord-ee7582389ece4fc89e6376d7c32e6984
Source dataset
uspto-grants-1990_10
Patent number
US04963564

Reaction notes

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