Synephrine → N-[(4-chlorophenyl)methyl]-6-[[[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-methyl-amino]methyl]-1-methyl-4-oxo-quinoline-3-carboxamide

HRID 1068009

Reaktionsgleichung

Reaktionsgleichung von HRID 1068009
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21]Cl)[CH:17]=3)[N:12]([CH3:23])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:35][NH:36][CH2:37][CH:38]([OH:46])[C:39]1[CH:40]=[CH:41][C:42]([OH:45])=[CH:43][CH:44]=1>CN(C=O)C.ClCCl>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][N:36]([CH2:37][CH:38]([OH:46])[C:39]4[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=4)[CH3:35])[CH:17]=3)[N:12]([CH3:23])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 7172SynephrineHCID 81531DiisopropylethylamineHCID 21192571N-(4-Chlorobenzyl)-6-(chloromethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide

Produkt 1

HCID 9849068N-[(4-chlorophenyl)methyl]-6-[[[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-methyl-amino]methyl]-1-methyl-4-oxo-quinoline-3-carboxamideAusbeute 74,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of N-(4-chlorobenzyl)-6-(chloromethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide (0.09 gm) from Preparation No. 35 in dry DMF (2 mL) containing diisopropylethylamine (0.07 mL) is treated with synephrine (0.05 gm). The reaction mixture is stirred overnight. The reaction mixture is diluted with dichloromethane (50 mL) and washed with water (2×10 mL), brine (10 mL), dried (Na2SO4) and concentrated under reduced pressure. The residue is purified by flash column chromatography eluting with 3% to 6% methanol in dichloromethane and then by recrystallization from toluene to afford 0.09 gm of the title compound as a tan solid.

Aufarbeitung

  1. washwashed with water (2×10 mL), brine (10 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by flash column chromatography
  5. washeluting with 3% to 6% methanol in dichloromethane
  6. customby recrystallization from toluene

Quellen und Nachweise

ORD-Eintrag
ord-5a0bd78eeaa84841a4c8b0f8c058ad95
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248739B1

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