Lithium Hydroxide → 2-(4-Benzylpiperazin-1-yl)benzoic acid

HRID 228109Notes

Reaction equation

HRID 228109 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=2[C:16]([O:18]C)=[O:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.O>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=2[C:16]([OH:18])=[O:17])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 21935101Methyl 2-[4-benzylpiperazinyl]benzoate

Product 1

HCID 219351932-(4-Benzylpiperazin-1-yl)benzoic acidYield 93.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a 150 mL round-bottomed flask equipped with magnetic stirring was added methyl 2-[4-benzylpiperazinyl]benzoate (Preparation XIII) (2.3 g, 7.4 mmol) in THF (60 mL). A soln of LiOH (Aldrich) (940 mg, 22 mmol) in H2O (20 mL), was added and the reaction mixture was heated at 60° C. for 12 h. After cooling to RT, the reaction mixture was concentrated in vacuo and diluted with EtOAc (100 mL). A 10% soln of citric acid (25 mL) was added, the organic layer was separated and the aqueous layer was extracted with EtOAc (2×25 mL). The organic layers were combined, washed with H2O, satd NaCl, dried over Na2SO4, filtered and concentrated in vacuo to afford 2-[4-benzylpiperazinyl]benzoic acid as a white solid (2.05 g). MS (ESI, pos. ion) m/z: 297 (M+H). Calc'd for C18H20N2O2: 296.15: 296.15.

Workup

  1. customTo a 150 mL round-bottomed flask equipped
  2. temperatureAfter cooling to RT
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. additiondiluted with EtOAc (100 mL)
  5. additionA 10% soln of citric acid (25 mL) was added
  6. customthe organic layer was separated
  7. extractionthe aqueous layer was extracted with EtOAc (2×25 mL)
  8. washwashed with H2O
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-618bbebec5f14112b114cf8e7b7006b4
Source dataset
uspto-grants-2009_07
Patent number
US07560460B2

Reaction notes

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