Sodium Hydroxide → N-(2-[2-Chlorophenyl]-propyl)-N-(2-chloro-3-trifluoromethylbenzyl)-3-(3-carboxymethylenephenoxy)propylamine, hydrochloride

HRID 902725Notes

Reaction equation

HRID 902725 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:38])[CH2:9][N:10]([CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH2:28][C:29](=[CH:33][C:34]([O:36]C)=[O:35])[CH:30]=[CH:31][CH:32]=1)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[C:13]=1[Cl:22].[OH-].[Na+]>CO.O>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:38])[CH2:9][N:10]([CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH2:28][C:29](=[CH:33][C:34]([OH:36])=[O:35])[CH:30]=[CH:31][CH:32]=1)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:19])[F:21])[C:13]=1[Cl:22]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69253617N-(2-[2-Chlorophenyl]-propyl)-N-(2-chloro-3-trifluoromethylbenzyl)-3-(3-carbomethoxymethylenephenoxy)propylamine

Product 1

HCID 131726846N-(2-[2-Chlorophenyl]-propyl)-N-(2-chloro-3-trifluoromethylbenzyl)-3-(3-carboxymethylenephenoxy)propylamine, hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of N-(2-[2-Chlorophenyl]-propyl)-N-(2-chloro-3-trifluoromethylbenzyl)-3-(3-carbomethoxymethylenephenoxy)propylamine (80 mg, 0.14 mmole) in 5 mL of MeOH was treated with 1 mL of H2O and 0.5 mL of 2.5N NaOH, and heated to 500 for 30 minutes. The reaction was diluted with H2O, and acidified to pH 4, and extracted with EtOAc. The extracts were washed with H2O, dried, and the solvent removed. The residue was dissolved in Et2O, a small amount of isopropanol was added, and treated with 4N HCl in dioxane. The precipitated solid was filtered, washed with Et2O and dried, and gave the titled compound, 65 mg (81%). MS (ESI) 554 (MH+).

Workup

  1. temperatureheated to 500 for 30 minutes
  2. extractionextracted with EtOAc
  3. washThe extracts were washed with H2O
  4. customdried
  5. customthe solvent removed
  6. dissolutionThe residue was dissolved in Et2O
  7. additiona small amount of isopropanol was added
  8. additiontreated with 4N HCl in dioxane
  9. filtrationThe precipitated solid was filtered
  10. washwashed with Et2O
  11. customdried

Sources & evidence

ORD record
ord-f6a5e25b14c74251a7057206edb13f4b
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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