Sulfuric Acid → [3-(4-Ethyl-piperazin-1-yl)-phenyl]-methyl-amine

HRID 912252Notes

Reaction equation

HRID 912252 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:10]=[C:11]([N:15](C)[C:16](=O)C)[CH:12]=[CH:13][CH:14]=2)[CH2:5][CH2:4]1)[CH3:2].S(=O)(=O)(O)O.[OH-].[Na+]>O>[CH2:1]([N:3]1[CH2:4][CH2:5][N:6]([C:9]2[CH:10]=[C:11]([NH:15][CH3:16])[CH:12]=[CH:13][CH:14]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 59245018N-[3-(4-Ethyl-piperazin-1-yl)-phenyl]-N-methyl-acetamide

Product 1

HCID 59244590[3-(4-Ethyl-piperazin-1-yl)-phenyl]-methyl-amineYield 86.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To N-[3-(4-ethyl-piperazin-1-yl)-phenyl]-N-methyl-acetamide (104.9 mg) obtained in Step C, water (2 ml) and concentrated sulfuric acid (0.4 ml) were added, followed by stirring at 80° C. for 8 hours. To this, 5M-NaOH aqueous solution was added, to adjust the pH to 9, followed by extraction with ethyl acetate (10 ml×2), and the organic layer was dried over sodium sulfate. The sodium sulfate was filtered off, followed by purification by silica gel column chromatography (dichloromethane/methanol=20/1 to 10/1), to obtain the desired compound (76.1 mg, 86%).

Workup

  1. extractionfollowed by extraction with ethyl acetate (10 ml×2)
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. filtrationThe sodium sulfate was filtered off
  4. customfollowed by purification by silica gel column chromatography (dichloromethane/methanol=20/1 to 10/1)

Sources & evidence

ORD record
ord-f4061eb4b14d4c32adc1bfbf6335dcb5
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

Loading…