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 1088710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1088710
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]

Komponenten

4

Edukt 2

HCID 113340552-Bromo-1-(4-hydroxy-3-(hydroxymethyl)phenyl)ethan-1-oneHCID 22161747N-[6-[3-(2-Pyridinyl)propoxy]hexyl]benzenemethanamine

Produkt 1

HCID 221617591-[4-Hydroxy-3-(hydroxymethyl)phenyl]-2-[(phenylmethyl)[6-[3-(2-pyridinyl)propoxy]hexyl]amino]ethanoneAusbeute 67,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-7e4b4c39db4d4405a1de85bd387be40b
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04963564

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