Sodium Hydroxide → 3-[4-(3-Cyano-phenyl)-piperazin-1-ylmethyl]-benzoic acid

HRID 1468162

Reaction equation

HRID 1468162 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]#[N:24])[CH:18]=3)[CH2:13][CH2:12]2)[CH:5]=1.[OH-].[Na+]>C1COCC1.CO>[C:23]([C:19]1[CH:18]=[C:17]([N:14]2[CH2:13][CH2:12][N:11]([CH2:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:25])=[O:2])[CH2:16][CH2:15]2)[CH:22]=[CH:21][CH:20]=1)#[N:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 675081903-[4-(3-Cyano-phenyl)-piperazin-1-ylmethyl]-benzoic acid methyl ester

Product 1

HCID 675074743-[4-(3-Cyano-phenyl)-piperazin-1-ylmethyl]-benzoic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Dissolve 3-[4-(3-cyano-phenyl)-piperazin-1-ylmethyl]-benzoic acid methyl ester into 10 mL of 1:1 THF/MeOH and add 2 mL of 15% NaOH. Stir the mixture overnight and concentrate to dryness. Dissolve the residue in 5% HCl and apply to Dowex column. Rinse the resin with 2×20 mL H2O, 2×20 mL MeOH and 2×20 mL of dichloromethane. Liberate the basic residues by washing the resin with 3×20 mL of 10% NH3/MeOH to give 0.26 g 3-[4-(3-cyano-phenyl)-piperazin-1-ylmethyl]-benzoic acid as a white solid. 1H NMR indicates some contamination with starting amine. The crude intermediate is carried on without further purification.

Workup

  1. concentrationconcentrate to dryness
  2. dissolutionDissolve the residue in 5% HCl
  3. washRinse the resin with 2×20 mL H2O, 2×20 mL MeOH and 2×20 mL of dichloromethane
  4. washby washing the resin with 3×20 mL of 10% NH3/MeOH

Sources & evidence

ORD record
ord-99acd1a56d654399a9a9ef07954e96d2
Source dataset
uspto-grants-2015_04
Patent number
US09000154B2

Linked notes

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