Hydrochloric Acid → 4-(4-Methylpiperazin-1-yl)benzoic acid

HRID 1177935

Reaction equation

HRID 1177935 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:19])[C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:8][CH:7]=1.O.Cl>C1COCC1.O>[CH3:18][N:15]1[CH2:14][CH2:13][N:12]([C:9]2[CH:10]=[CH:11][C:6]([C:5]([OH:19])=[O:4])=[CH:7][CH:8]=2)[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 1472668Methyl 4-(4-methylpiperazin-1-yl)benzoate

Product 1

HCID 7365324-(4-Methylpiperazin-1-yl)benzoic acidYield 85.13%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

LiOH (67 mg, 1.6 mmol) was added to a stirred solution 4-(4-methyl-piperazin-1-yl)-benzoic acid methyl ester (124 mg, 0.73 mmol) in THF:H2O (1:1, 4 mL), and the resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure to get the residue. Cold water was then added and acidified it with 10% aqueous HCl and concentrated under reduced pressure to afford 116 mg (85.13% yield) of 4-(4-methyl-piperazin-1-yl)-benzoic acid. 1H NMR (DMSO-D2O): δ 7.8 (d, 2H), 7.0 (d, 2H), 3.4 (s, 4H), 2.8 (s, 4H), 2.4 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto get the residue
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e3ae7b1d8a90423cacf494b73e07d6df
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Linked notes

Loading…