Sodium Iodide → Methyl 4-((4-methylpiperazin-1-yl)methyl)benzoate

HRID 1455057Notes

Reaction equation

HRID 1455057 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Cl)=[CH:6][CH:5]=1.[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[I-].[Na+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:17]2[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH2:16]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 5238Sodium Iodide2×HCID 36664Methyl 4-(chloromethyl)benzoateHCID 531671-Methylpiperazine2×

Product 1

HCID 782222Methyl 4-((4-methylpiperazin-1-yl)methyl)benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

4-Chloromethylbenzoic acid methyl ester (1.66 g), 1-methylpiperazine (1.8 g) and sodium iodide (0.67 g) were added into acetone (50 ml). The reaction mixture was stirred at 60° C. for 9 hours. More 1-methylpiperazine (0.9 g) and sodium iodide (0.34 g) were added and after stirring additional 1½ hours at 60° C. the reaction mixture was allowed to cool into room temperature. The mixture was filtered and acetone was evaporated. The residue was dissolved in ethyl acetate and washed with water. The solvent was dried with NaSO4 and evaporated to yield 4-(4-methyl-piperazin-1-ylmethyl)benzoic acid methyl ester. 1H NMR (300 MHz, d6-DMSO) δ: 2.18 (s, 3H), 2.37 (bs, 8H), 3.53 (s, 2H), 3.84 (s, 3H), 7.44 (d, 2H, J 8.1 Hz), 7.91 (d, 2H, J 8.2 Hz).

Workup

  1. stirringafter stirring additional 1½ hours at 60° C. the reaction mixture
  2. temperatureto cool into room temperature
  3. filtrationThe mixture was filtered
  4. customacetone was evaporated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with water
  7. dry with materialThe solvent was dried with NaSO4
  8. customevaporated

Sources & evidence

ORD record
ord-15ebb11e3db94c45a026918c2779850b
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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