Hydrochloric Acid → 3-(4-(4-Methoxyphenyl)piperidin-1-yl)-2-phenylquinoxaline-6-carboxylic acid

HRID 716898Notes

Reaction equation

HRID 716898 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]3[C:16]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[N:17][C:18]4[C:23]([N:24]=3)=[CH:22][C:21]([C:25]([O:27]C)=[O:26])=[CH:20][CH:19]=4)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[OH-].[Na+].Cl>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]3[C:16]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[N:17][C:18]4[C:23]([N:24]=3)=[CH:22][C:21]([C:25]([OH:27])=[O:26])=[CH:20][CH:19]=4)[CH2:11][CH2:10]2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67041989Methyl 3-(4-(4-methoxyphenyl)piperidin-1-yl)-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 509920253-(4-(4-Methoxyphenyl)piperidin-1-yl)-2-phenylquinoxaline-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-(4-(4-methoxyphenyl)piperidin-1-yl)-2-phenylquinoxaline-6-carboxylate (179.6 mg, 0.36 mmol, 1.00 equiv, 90%) in methanol (17 mL) was added a solution of sodium hydroxide (80 mg, 2.00 mmol, 5.00 equiv) in water (2 mL) dropwise with stirring. The resulting solution was stirred for 7 h at 50° C. in an oil bath, then the pH of the solution was adjusted to 3-4 with 1N hydrochloric acid. The resulting mixture was concentrated under vacuum, followed by washing with methanol yielding 81.9 mg (50%) of 3-(4-(4-methoxyphenyl)piperidin-1-yl)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid.

Workup

  1. stirringThe resulting solution was stirred for 7 h at 50° C. in an oil bath
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. washby washing with methanol yielding 81.9 mg (50%) of 3-(4-(4-methoxyphenyl)piperidin-1-yl)-2-phenylquinoxaline-6-carboxylic acid as a yellow solid

Sources & evidence

ORD record
ord-c8062b4f228d48708912cbdffceb99b4
Source dataset
uspto-grants-2015_11
Patent number
US09193693B2

Reaction notes

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