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

HRID 1068009

Reaction equation

HRID 1068009 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5a0bd78eeaa84841a4c8b0f8c058ad95
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Linked notes

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