Sodium Hydroxide → 2-Methyl-4-(4-methylpiperazin-1-yl)benzoic acid

HRID 1803867Notes

Reaction equation

HRID 1803867 reaction equation
C[O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[CH:6][C:5]=1[CH3:17].[OH-].[Na+]>>[CH3:17][C:5]1[CH:6]=[C:7]([N:10]2[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15]2)[CH:8]=[CH:9][C:4]=1[C:3]([OH:18])=[O:2]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 54298739Methyl 2-methyl-4-(4-methylpiperazin-1-yl)benzoate

Product 1

HCID 537293462-Methyl-4-(4-methylpiperazin-1-yl)benzoic acid

Conditions

Temperature
40 °C

Procedure

To a solution of 2-methyl-4-(4-methyl-piperazin-1-yl)-benzoic acid methyl ester (660 mg, 2.66 mmol) in MeOh (4 ml), 2M NaOH (4 ml, 8 mmol) was added. The reaction was heated for 3 hours at 40° C. until HPLC revealed the disappearance of the starting-material. The solvent was removed under reduced pressure and the solution was diluted with water and neutralized to pH 7 with aqueous 25% HCl. The precipitate was filtrated and washed with Et2O to afford the desired final compound as with solid (400 mg, 64%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe solution was diluted with water and neutralized to pH 7 with aqueous 25% HCl
  3. filtrationThe precipitate was filtrated
  4. washwashed with Et2O

Sources & evidence

ORD record
ord-acac834213ba4c57aeb3d83a0fa7fbe8
Source dataset
uspto-grants-2013_01
Patent number
US08354399B2

Reaction notes

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