Methanol → Methyl 2-(4-(4-methylpiperazin-1-yl)phenyl)acetate

HRID 1896253Notes

Reaction equation

HRID 1896253 reaction equation
S(Cl)(Cl)=O.[CH3:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=[O:20])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.[CH3:22]O>>[CH3:5][N:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:13]=[CH:14][C:15]([CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:16][CH:17]=2)[CH2:10][CH2:11]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 28807075[4-(4-Methyl-piperazin-1-yl)-phenyl]-acetic acid

Product 1

HCID 59903719Methyl 2-(4-(4-methylpiperazin-1-yl)phenyl)acetate

Procedure

Thionyl chloride (0.32 g, 2.77 mmol) was added dropwise to a suspension of 2-(4-(4-methylpiperazin-1-yl)phenyl)acetic acid (2.60 g, 11.1 mmol) in MeOH (30 ml) at 0° C. and refluxed for 5 h. The reaction mixture was concentrated and the residue was dissolved in water, made alkaline with saturated sodium bicarbonate solution up to pH˜8 and extracted with DCM. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated to dryness to get the crude compound. The crude was purified by column chromatography over neutral alumina using 4% MeOH in DCM as eluent to afford 250 mg of methyl 2-(4-(4-methylpiperazin-1-yl)phenyl)acetate as brown color solid.

Workup

  1. temperaturerefluxed for 5 h
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in water
  4. extractionextracted with DCM
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customto get the crude compound
  10. customThe crude was purified by column chromatography over neutral alumina using 4% MeOH in DCM as eluent

Sources & evidence

ORD record
ord-f0aef957b2ca485f80fb4a234ed8eb7f
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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