Hydrochloric Acid → 1-((2-(4-Chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

HRID 1025404Notes

Reaction equation

HRID 1025404 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:25])=[C:11]([CH2:13][N:14]3[CH2:19][CH2:18][CH:17]([C:20]([O:22]CC)=[O:21])[CH2:16][CH2:15]3)[N:12]=2)=[CH:4][CH:3]=1.[Li+].[OH-].CO.Cl>O1CCOCC1.O.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:25])=[C:11]([CH2:13][N:14]3[CH2:19][CH2:18][CH:17]([C:20]([OH:22])=[O:21])[CH2:16][CH2:15]3)[N:12]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 42116034Ethyl 1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylate

Product 1

HCID 209671331-((2-(4-Chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylate (1.0 g, 2.7 mmole) and LiOH (240 mg, 10 mmol) were mixed with MeOH (5 mL), THF (5 ml) and Water (2 mL). The mixture was stirred at 50 for 2 h. 4N HCl in dioxane (3 mL) was added the reaction solution was stirred at room temperature for another 1 h. The solvent was removed under vacuum to give 1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid as white solid, the crude product was used without purification.

Workup

  1. stirringwas stirred at room temperature for another 1 h
  2. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-0ca987370db645dc8427ef5dab79dcb8
Source dataset
uspto-grants-2014_05
Patent number
US08729081B2

Reaction notes

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