Hydrochloric Acid → 1-{2-[1-(3,4-Dichlorophenyl)-5-methyl-1H-pyrazol-3-yloxy]ethyl}pyrrolidin-3-amine

HRID 220003Notes

Reaction equation

HRID 220003 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][CH:20]([NH:23]C(=O)C)[CH2:19]3)=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[OH-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][CH:20]([NH2:23])[CH2:19]3)=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57919736N-(1-(2-(1-(3,4-dichlorophenyl)-5-methyl-1H-pyrazol-3-yloxy)ethyl)pyrrolidin-3-yl)acetamide

Product 1

HCID 115955611-{2-[1-(3,4-Dichlorophenyl)-5-methyl-1H-pyrazol-3-yloxy]ethyl}pyrrolidin-3-amineYield 90.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of N-(1-(2-(1-(3,4-dichlorophenyl)-5-methyl-1H-pyrazol-3-yloxy)ethyl)pyrrolidin-3-yl)acetamide (0.1 g, 0.25 mmol) in water (2 ml) and 6N aqueous solution of HCl (2 ml) was refluxed for 5 hrs. The mixture was basified with 20% aqueous solution of NaOH and extracted with dichloromethane. The combined organic solutions was washed with water, dried over Na2SO4, filtered and evaporated to dryness yielding 80 mg of 1-{2-[1-(3,4-Dichlorophenyl)-5-methyl-1H-pyrazol-3-yloxy]ethyl}pyrrolidin-3-amine as an oil

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined organic solutions was washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-9e7e6807a3144036a97a857a6c236417
Source dataset
uspto-grants-2012_06
Patent number
US08202872B2

Reaction notes

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