Hydrochloric Acid → [4-(4-Benzyloxy-benzoyl)-piperidin-1-yl]-acetic acid

HRID 713465Notes

Reaction equation

HRID 713465 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12](=[O:27])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)C.[OH-].[Na+].Cl>O.C(O)C>[CH2:20]([O:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]([CH:9]2[CH2:8][CH2:7][N:6]([CH2:5][C:4]([OH:28])=[O:3])[CH2:11][CH2:10]2)=[O:27])=[CH:14][CH:15]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71227181HCID 71227181, compound

Product 1

HCID 71226877[4-(4-Benzyloxy-benzoyl)-piperidin-1-yl]-acetic acidYield 156.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of [4-(4-benzyloxy-benzoyl)-piperidin-1-yl]-acetic acid ethyl ester (180 mg, 0.47 mmol) in water (2 mL) and ethanol (2 mL) was added a 4N solution of NaOH (0.24 mL, 0.94 mmol). The reaction was heated up to 40° C. for 3 hours. The reaction was acidified to pH 3 using 1N HCl, then the solvent was then evaporated under vacuum to afford the crude title compound (260 mg). LRMS m/z: ES+=354.4 (M+H), retention time 1.11.

Workup

  1. customthe solvent was then evaporated under vacuum

Sources & evidence

ORD record
ord-9e72f2ebcf484a19a3497590c84aa291
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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