Formaldehyde → Diethyl 2-(4-(4-methylpiperazin-1-yl)benzyl)-2-methylmalonate

HRID 2176911Notes

Reaction equation

HRID 2176911 reaction equation
[N:1]1([C:7]2[CH:25]=[CH:24][C:10]([CH2:11][C:12]([CH3:23])([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH2:26]=O>C(O)=O>[CH3:26][N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:8]=[CH:9][C:10]([CH2:11][C:12]([CH3:23])([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:24][CH:25]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 67382829Diethyl 2-(4-(piperazin-1-yl)benzyl)-2-methylmalonate

Product 1

HCID 67383064Diethyl 2-(4-(4-methylpiperazin-1-yl)benzyl)-2-methylmalonateYield 86.8%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of diethyl 2-(4-(piperazin-1-yl)benzyl)-2-methylmalonate (500 mg, 1.43 mmol), formaldehyde (2 ml) and formic acid (2 ml) was heated at reflux for 2 h. The reaction mixture was concentrated and partitioned between saturated sodium bicarbonate solution and ethyl acetate. The organic layer was separated and washed with water, brine solution, dried over anhydrous sodium sulfate, filtered and concentrated to afford 400 mg (86.8%) of diethyl 2-(4-(4-methylpiperazin-1-yl)benzyl)-2-methylmalonate as brown oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. concentrationThe reaction mixture was concentrated
  4. custompartitioned between saturated sodium bicarbonate solution and ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with water, brine solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-67d9c96ce0b24302964936d07659532a
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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