Formaldehyde → Diethyl 2-methyl-2-(4-(4-methylpiperazin-1-yl)phenyl)malonate

HRID 2176907Notes

Reaction equation

HRID 2176907 reaction equation
[CH2:1]=O.[CH3:3][C:4]([C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:17][CH:16]=1)([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6]>C(O)=O>[CH3:3][C:4]([C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:22][CH2:23][N:24]([CH3:1])[CH2:25][CH2:26]2)=[CH:17][CH:16]=1)([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 67382666Diethyl 2-methyl-2-(4-(piperazin-1-yl)phenyl)malonate

Product 1

HCID 67382777Diethyl 2-methyl-2-(4-(4-methylpiperazin-1-yl)phenyl)malonateYield 70%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of formaldehyde (2 ml), formic acid (2 ml) and diethyl 2-methyl-2-(4-(piperazin-1-yl)phenyl)malonate (4.80 g, 14.4 mmol) was heated at reflux for 2 h and the reaction mixture was concentrated under reduced pressure. Saturated sodium bicarbonate solution was added and extracted with ethyl acetate. The organic layer was washed with water, brine solution, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford 3.50 g (70.0%) of diethyl 2-methyl-2-(4-(4-methylpiperazin-1-yl)phenyl)malonate as brown oily liquid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. additionSaturated sodium bicarbonate solution was added
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water, brine solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-afb045b4206841108a4ff52be4d4d729
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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