Triethylamine → 2-Methoxy-4-[(4-methylpiperazin-1-yl)methyl]benzoic acid methyl ester

HRID 632505Notes

Reaction equation

HRID 632505 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:15][O:16][C:17](=[O:28])[C:18]1[CH:23]=[CH:22][C:21]([CH2:24]Br)=[CH:20][C:19]=1[O:26][CH3:27]>C(O)C>[CH3:15][O:16][C:17](=[O:28])[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:20][C:19]=1[O:26][CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 11288398Methyl 4-(bromomethyl)-2-methoxybenzoate

Product 1

HCID 1178889242-Methoxy-4-[(4-methylpiperazin-1-yl)methyl]benzoic acid methyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To 100 mL of ethanol were added 10.0 g of 1-methylpiperazine and 20.2 g of triethylamine. To the mixture cooled with ice, 25 mL of a solution of 24.6 g of 4-(bromomethyl)-2-methoxy-benzoic acid methyl ester in ethanol was added dropwise. The mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated. To the residue, 75 mL of water and 250 mL of methylene chloride were added, and the organic layer was separated. The obtained organic layer was dried over Na2SO4 and concentrated. The residue was purified by amino-silica gel column chromatography (heptane/AcOEt system) to give 22.4 g of the title compound (85% yield).

Workup

  1. additionwas added dropwise
  2. concentrationThe reaction mixture was concentrated
  3. additionTo the residue, 75 mL of water and 250 mL of methylene chloride were added
  4. customthe organic layer was separated
  5. dry with materialThe obtained organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by amino-silica gel column chromatography (heptane/AcOEt system)

Sources & evidence

ORD record
ord-ee31b6255db64fbd9a3ebe8ab054d666
Source dataset
uspto-grants-2016_04
Patent number
US09321752B2

Reaction notes

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