Hydrochloric Acid → 3-(4-Isobutyrylpiperazine-1-carbonyl)benzoic acid

HRID 415312Notes

Reaction equation

HRID 415312 reaction equation
[C:1]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=2)[C:17]([O:19]C)=[O:18])=[O:13])[CH2:8][CH2:7]1)(=[O:5])[CH:2]([CH3:4])[CH3:3].O.[OH-].[Li+].Cl>O.O1CCCC1>[C:1]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=2)[C:17]([OH:19])=[O:18])=[O:13])[CH2:8][CH2:7]1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 66621314Methyl 3-(4-isobutyrylpiperazine-1-carbonyl)benzoate

Product 1

HCID 666215403-(4-Isobutyrylpiperazine-1-carbonyl)benzoic acidYield 92.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(4-isobutyrylpiperazine-1-carbonyl)benzoate (1.25 g, 3.9 mmol) in water (10 mL) and tetrahydrofuran (10 mL) at 0° C., lithium hydroxide monohydrate (250 mg, 6 mmol) was added. The mixture was stirred at that temperature for 2 h. The resulting mixture was neutralized to pH=5 with hydrochloric acid, and extracted with ethyl acetate (100 mL×4) and concentrated to obtain a white solid of 3-(4-isobutyrylpiperazine-1-carbonyl)benzoic acid (1.1 g, yield 76%). LC-MS (ESI) m/z: 305 (M+1)+.

Workup

  1. extractionextracted with ethyl acetate (100 mL×4)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d28db13e59fd42ed94f3a4ab7f14e2c4
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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