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

HRID 2170868Notes

Reaction equation

HRID 2170868 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=3)[C:18]([O:20]C)=[O:19])=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[OH-].[Na+].O1CCCC1.Cl>CO>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=3)[C:18]([OH:20])=[O:19])=[O:14])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 67168960HCID 67168960, compound

Product 1

HCID 671691753-(4-(4-Chlorophenoxy)piperidine-1-carbonyl)benzoic acidYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 3-(4-(4-chlorophenoxy)piperidine-1-carbonyl)benzoate (301 mg, 0.81 mmol, Step-1), 2M sodium hydroxide aqueous solution (2 mL), tetrahydrofuran (2 mL), and methanol (2 mL) was stirred at 60° C. for 2 hours. The mixture was acidified by 2M aqueous hydrochloric acid solution and extracted with ethyl acetate (10 mL). The organic layer was dried over sodium sulfate, and concentrated under reduced pressure to give 270 mg (93% yield) of the title compound as a white solid.

Workup

  1. extractionextracted with ethyl acetate (10 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f612142bd8244adf803ce59a6623de26
Source dataset
uspto-grants-2015_06
Patent number
US09051296B2

Reaction notes

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