Hydrochloric Acid → [4-(5-Phenyl[1,3,4]oxadiazol-2-yl)-piperidin-1-yl]-acetic acid

HRID 713412Notes

Reaction equation

HRID 713412 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[O:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:15][N:16]=2)[CH2:8][CH2:7]1)C.[OH-].[Na+].Cl>CCO.O>[C:17]1([C:14]2[O:13][C:12]([CH:9]3[CH2:8][CH2:7][N:6]([CH2:5][C:4]([OH:23])=[O:3])[CH2:11][CH2:10]3)=[N:16][N:15]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71227094[4-(5-Phenyl-[1,3,4]oxadiazol-2-yl)-piperidin-1-yl]-acetic acid ethyl ester

Product 1

HCID 71227151[4-(5-Phenyl[1,3,4]oxadiazol-2-yl)-piperidin-1-yl]-acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of [4-(5-phenyl-[1,3,4]oxadiazol-2-yl)-piperidin-1-yl]-acetic acid ethyl ester in EtOH was added NaOH (36.6 mg, 0.916 mmol, 2 eq) in water (0.421 mL). The mixture was stirred for 4 h and the cloudy suspension was treated dropwise with 2.3 mL of 1N HCl until pH ˜7. The solvent was evaporated in vacuo to yield the title compound in quantitative yield used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.99 (d, J=7.58 Hz, 2H) 7.56-7.64 (m, 3H) 2.92-3.08 (m, 5H) 2.29-2.42 (m, 2H) 2.01-2.12 (m, 2H) 1.80-1.96 (m, 2H). MS (m/z, MH+): 288.3.

Workup

  1. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-23c4148c88d544319d750679b6b5e93a
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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