Water → (+/-)-4-(4-Chlorobenzyl)-2-[(4-chloro-2-methoxyphenoxy)methyl]morpholine oxalic acid salt

HRID 1017249

Reaction equation

HRID 1017249 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][O:10][CH:9]([CH2:13]Cl)[CH2:8]2)=[CH:4][CH:3]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([O:25][CH3:26])[CH:19]=1.[O-]CC.[K+].C1OCCOCCOCCOCCOCCOC1.[OH2:49]>C1(C)C=CC=CC=1>[C:20]([OH:25])(=[O:10])[C:21]([OH:24])=[O:49].[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][O:10][CH:9]([CH2:13][O:24][C:21]3[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][C:20]=3[O:25][CH3:26])[CH2:8]2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 962WaterHCID 280504-ChloroguaiacolHCID 2855718-Crown-6HCID 11345975Morpholine, 2-(chloromethyl)-4-[(4-chlorophenyl)methyl]-HCID 23670592Potassium ethoxide

Product 1

HCID 69687298(+/-)-4-(4-Chlorobenzyl)-2-[(4-chloro-2-methoxyphenoxy)methyl]morpholine oxalic acid salt

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of (±)-4-(4-chlorobenzyl)-2-chloromethyimorphoiine (10.0 g 38.5 mmol), 4-chloro-2-methoxyphenol (9.0 g, 58 mmol), potassium ethoxide (6.5 g, 77 mmol), and 18-crown-6 (10.2 g, 38.5) was refluxed in toluene (100 ml) for 34 h. Water (200 ml) was added and the phases were separated. Drying and evaporation of the toluene phase was followed by column chromatography on silica gel with 3% ethanol in dichloromethane as eluent. The free base was dissolved in ether and precipitated with oxalic acid to give the title compound. Yield 10.3 g, 57%, mp 133-139° C.

Workup

  1. customthe phases were separated
  2. customDrying
  3. customevaporation of the toluene phase
  4. dissolutionThe free base was dissolved in ether
  5. customprecipitated with oxalic acid

Sources & evidence

ORD record
ord-c4b63b09980c4d7aa532036efc2c466f
Source dataset
uspto-grants-2002_11
Patent number
US06479491B1

Linked notes

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