Hydrochloric Acid → HCID 71226873, compound

HRID 713439Notes

Reaction equation

HRID 713439 reaction equation
C([O:3][C:4](=[O:20])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[O:13])[CH2:8][CH2:7]1)C.C(O)C.[OH-].[Na+].Cl>O>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:12]([CH:9]1[CH2:8][CH2:7][N:6]([CH2:5][C:4]([OH:20])=[O:3])[CH2:11][CH2:10]1)=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 71227120HCID 71227120, compound

Product 1

HCID 71226873HCID 71226873, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of compound [4-(pyridine-2-carbonyl)-piperidin-1-yl]-acetic acid ethyl ester (198 mg, 0.72 mmol), in water (4 mL) and ethanol (4 mL) and was added 4N sodium hydroxide (0.36 mL, 1.43 mmol). The reaction was stirred at 25° C. for 48 hours and then heated at 40° C. for 3 hours. The reaction mixture was acidified with 1N HCl to pH 3 and the solvent was removed under vacuum. The residue was co-evaporated 3 times with acetonitrile to afford the title compound (178 mg). The crude product was used directly in the next step without subsequent purification. MS m/z ES+=248.8 (M+H), retention time 1.66.

Workup

  1. temperatureheated at 40° C. for 3 hours
  2. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-36c47959b67946329ad294a529b53303
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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