Sodium Hydroxide → 3-Fluoro-4-(4-methylpiperazin-1-yl)benzoic acid

HRID 906066Notes

Reaction equation

HRID 906066 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)[C:5]([O:7]C)=[O:6].[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57703850Methyl 3-Fluoro-4-(4-methyl-1-piperazinyl)benzoate

Product 1

HCID 184138543-Fluoro-4-(4-methylpiperazin-1-yl)benzoic acidYield 43.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To methyl 3-fluoro-4-(4-methylpiperazin-1-yl)benzoate (1.80 g, 7.13 mmol) in methanol (40 ml) was added 1 M sodium hydroxide (25 ml, 25.0 mmol). The solution was stirred at 50° C. for 3 h, at which point the mixture was concentrated. The residue was diluted with water (10 ml) and the pH adjusted to 6 with 1 N hydrochloric acid. The resultant precipitate was collected by filtration and dried in vacuo to afford (733 mg, 43%) of 3-fluoro-4-(4-methylpiperazin-1-yl)benzoic acid. 1H NMR (400 MHz, CD3OD): 7.73-7.68 (d, 1H), 7.62-7.57 (d, 1H), 7.03-6.97 (m, 1H), 3.26-3.20 (m, 4H), 2.83-2.76 (m, 4H), 2.47 (s, 3H). MS (EI) for C12H15FN2O2: 239 (MH+).

Workup

  1. concentrationwas concentrated
  2. additionThe residue was diluted with water (10 ml)
  3. filtrationThe resultant precipitate was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-961d0c9bfe854ee4bba53985664a2aff
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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