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

HRID 1068009

反応式

HRID 1068009 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 9849068N-[(4-chlorophenyl)methyl]-6-[[[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-methyl-amino]methyl]-1-methyl-4-oxo-quinoline-3-carboxamide収率 74.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5a0bd78eeaa84841a4c8b0f8c058ad95
出典データセット
uspto-grants-2001_06
特許番号
US06248739B1

関連ノート

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