Hydrochloric Acid → N-(2,2-Diphenylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-3-(3-carboxyphenoxy)propylamine, hydrochloride

HRID 229120Notes

Reaction equation

HRID 229120 reaction equation
[C:1]1([CH:7]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:8][N:9]([CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([O:34]C)=[O:33])[CH:27]=2)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[C:12]=2[Cl:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>CO.O>[ClH:21].[C:36]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][N:9]([CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([OH:34])=[O:33])[CH:27]=2)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:18])([F:20])[F:19])[C:12]=2[Cl:21])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 577571333-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-2,2-diphenylethyl-amino]-propoxy}-benzoic acid methyl ester

Product 1

HCID 68861721N-(2,2-Diphenylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-3-(3-carboxyphenoxy)propylamine, hydrochlorideYield 81.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of N-(2,2-diphenylethyl)-N-(2-chloro-3-trifluoromethylbenzyl)-3-(3-carbomethoxyphenoxy)propylamine (65 mg, 0.11 mmol) in MeOH (5 mL), H2O (1 mL), and 2.5N NaOH (0.5 mL) was heated at 50° C. for 3 h. The reaction was cooled, diluted with H2O, acidified with 3N HCl to pH=4, and extracted with EtOAc. The extracts were dried and the solvent removed. The residue was dissolved in Et2O and treated with 4N HCl in dioxane. The precipatated solid was filtered, washed with Et2O, dried, and concentrated to yield the titled compound (27 mg, 42%). MS (ESI) 569 (M+H+).

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with EtOAc
  3. customThe extracts were dried
  4. customthe solvent removed
  5. dissolutionThe residue was dissolved in Et2O
  6. additiontreated with 4N HCl in dioxane
  7. filtrationThe precipatated solid was filtered
  8. washwashed with Et2O
  9. customdried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-4ffedcba687b4f168dd7a6ec750a5d3a
Source dataset
uspto-grants-2009_07
Patent number
US07560586B2

Reaction notes

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