Hydrochloric Acid → 3-[(4-methylcyclohexanecarbonyl)-(4-piperidyl)amino]-5-phenyl-thiophene-2-carboxylic Acid

HRID 73189Notes

Reaction equation

HRID 73189 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:8][C:9]=1[N:10]([C:17]([CH:19]1[CH2:24][CH2:23][CH:22]([CH3:25])[CH2:21][CH2:20]1)=[O:18])[CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:4].O.[Li+].[OH-].Cl>O1CCOCC1>[CH3:25][CH:22]1[CH2:21][CH2:20][CH:19]([C:17]([N:10]([CH:11]2[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]2)[C:9]2[CH:8]=[C:7]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[S:6][C:5]=2[C:3]([OH:4])=[O:2])=[O:18])[CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 59752320HCID 59752320, compound

Product 1

HCID 104102193-[(4-methylcyclohexanecarbonyl)-(4-piperidyl)amino]-5-phenyl-thiophene-2-carboxylic AcidYield 84%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-[(4-Methyl-cyclohexanecarbonyl)-piperidin-4-yl-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (20 mg, 0.045 mmol) was dissolved in a 4:1 mixture of dioxane:H2O (0.5 ml) and then LiOH 1N (135 ul, 0.135 mmol) was added. After 4 hours of stirring at room temperature, the reaction mixture was acidified to pH 3-4 with a 10% solution of hydrochloric acid and then the solvents were removed. It was further diluted in cold water (1 ml) and filtered out to give 16 mg (84%) of 3-[(4-Methyl-cyclohexanecarbonyl)-piperidin-4-yl-amino]-5-phenyl-thiophene-2-carboxylic acid (Compound 41).

Workup

  1. customthe solvents were removed
  2. additionIt was further diluted in cold water (1 ml)
  3. filtrationfiltered out

Sources & evidence

ORD record
ord-e29ab0d452fa48b58743ee156625d695
Source dataset
uspto-grants-2014_09
Patent number
US08829030B2

Reaction notes

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