Potassium Carbonate → 2-(4-Methylpiperazin-1-yl)benzaldehyde

HRID 1454399Notes

Reaction equation

HRID 1454399 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].F[C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=[O:18]>O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:15]2[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=2[CH:17]=[O:18])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 67970o-Fluorobenzaldehyde

Product 1

HCID 27955662-(4-Methylpiperazin-1-yl)benzaldehydeYield 97.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1-methylpiperazine (139.5 mL, 1.26 moles), potassium carbonate (145 g, 1.05 moles), and 2-fluorobenzaldehyde (73.7 mL, 0.7 moles) in water (700 mL) was heated at reflux for 18 hours. The solution was cooled to room temperature, extracted with methylene chloride (2×700 mL), and the combined organic layers were washed with water (2×700 mL). The organic layer was dried (MgSO4), filtered, and the solvent was removed in vacuo to afford 140 g of a dark oil. 1H NMR (400 MHz, CDCl3) 7.79 (dd, J=1.2, 7.9 Hz, 1H), 7.52 (td, J=1.5, 7.5 Hz, 1H), 7.11 (m, 2H), 3.12 (t, J=4.8 Hz, 4H), 2.63 (brs, 4H), 2.39 (s, 3H); 13C NMR (100 MHz, CDCl3) 191.6, 155.8, 135.2, 130.0, 128.9, 122.8, 119.2, 55.3, 54.1, 46.3.

Workup

  1. temperatureat reflux for 18 hours
  2. extractionextracted with methylene chloride (2×700 mL)
  3. washthe combined organic layers were washed with water (2×700 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-faa4b82ab0f0431ba1a3cdf304592be5
Source dataset
uspto-grants-2009_01
Patent number
US07479559B2

Reaction notes

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