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

HRID 1088710Notes

Reaction equation

HRID 1088710 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][O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][NH:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1>[OH:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][N:30]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][O: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 22161747N-[6-[3-(2-Pyridinyl)propoxy]hexyl]benzenemethanamine

Product 1

HCID 221617591-[4-Hydroxy-3-(hydroxymethyl)phenyl]-2-[(phenylmethyl)[6-[3-(2-pyridinyl)propoxy]hexyl]amino]ethanoneYield 67.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-bromo-1-[4-hydroxy-3-(hydroxymethyl)phenyl]ethanone (2.45 g), N-[6-[3-(2-pyridinyl)propoxy]hexyl]benzenemethanamine (3.26 g) and DEA (2.6 g) in THF (25 ml) was left at room temperature for 48 h. The precipitate was removed by filtration, the solvent was evaporated and the residual red oil was purified by FCC eluting with System B (95:5:1→90:10:1) to give the title compound as a pale yellow oil (3.32 g), t.l.c. (System A 80:20:1) Rf 0.21.

Workup

  1. customThe precipitate was removed by filtration
  2. customthe solvent was evaporated
  3. customthe residual red oil was purified by FCC
  4. washeluting with System B (95:5:1→90:10:1)

Sources & evidence

ORD record
ord-7e4b4c39db4d4405a1de85bd387be40b
Source dataset
uspto-grants-1990_10
Patent number
US04963564

Reaction notes

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