Water → 1-[(2,5-Dimethylphenyl)acetyl]-4-piperidinecarboxylic acid

HRID 2043730Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([C:18]([O:20]C)=[O:19])[CH2:14][CH2:13]1)=[O:11].O.[OH-].[Na+]>O1CCCC1.[Cl-].[Na+].O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=[O:19])[CH2:14][CH2:13]1)=[O:11]

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl 1-[(2,5-dimethylphenyl)acetyl]-4-piperidinecarboxylate (i.e. the product of Example 9, Step A) (4.95 g, 17.1 mmol) was dissolved in 20 mL of tetrahydrofuran, and 15 mL of water was added. With vigorous stirring the reaction mixture was cooled to 0° C., and 35 mL of a 1 N aqueous sodium hydroxide solution was added dropwise. The reaction mixture was stirred at room temperature for 1 h, diluted with 20 mL of brine, washed with diethyl ether (3×20 mL), and the aqueous phase was acidified with 1 N aqueous hydrochloric acid to pH 3-4. The precipitate was collected and dried to give 4.08 g of the title compound.

Workup

stirringThe reaction mixture was stirred at room temperature for 1 h
washwashed with diethyl ether (3×20 mL)
customThe precipitate was collected
customdried

Sources & evidence

ORD record: ord-b60fc8d3aaf14cb9aa068133d4cd1902
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586611B2

Reaction notes

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