N-Methylphenylethanolamine → N-(4-Chlorobenzyl)-6-{[(2-hydroxy-2-phenylethyl)(methyl)-amino]methyl}-1-methyl-4-oxo-1,4-dihydro-3quinolinecarboxamide

HRID 1068006

Reaktionsgleichung

Reaktionsgleichung von HRID 1068006
[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:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:3]=[CH:4][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:45])[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[CH3:35])[CH:17]=3)[N:12]([CH3:23])[CH:11]=2)=[O:9])=[CH:24][CH:25]=1

Komponenten

5

Edukt 3

HCID 913N-MethylphenylethanolamineHCID 81531DiisopropylethylamineHCID 21192571N-(4-Chlorobenzyl)-6-(chloromethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide

Produkt 1

HCID 21192531N-(4-Chlorobenzyl)-6-{[(2-hydroxy-2-phenylethyl)(methyl)-amino]methyl}-1-methyl-4-oxo-1,4-dihydro-3quinolinecarboxamideAusbeute 63,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A solution of N-(4-chlorobenzyl)-6-(chloromethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide (0.06 gm) from Preparation No. 35 in dry NMP (2 mL) containing diisopropylethylarnine (0.04 mL) is treated with α-(methylaminomethyl)-benzyl alcohol (0.04 gm). The reaction mixture is shaken at room temperature for 3 days then concentrated under reduced pressure. The residue is partioned between dichloromethane and water. The separated organic layer is washed with two additional portions of water, brine, dried (Na2SO4) and concentrated under reduced pressure. The residue is adsorbed onto silica and purified by flash column chromatography eluting with 2% to 6% methanol in dichloromethane and then by recrystallization from ethyl acetate-hexanes to afford 0.05 gm of the title compound as a white solid.

Aufarbeitung

  1. concentrationthen concentrated under reduced pressure
  2. washThe separated organic layer is washed with two additional portions of water, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. custompurified by flash column chromatography
  6. washeluting with 2% to 6% methanol in dichloromethane
  7. customby recrystallization from ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-69358d5342f5415e8d81080eb6212e47
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248739B1

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