Water → 3-Pyridinecarboxylic acid, 6-(4-amino-1-piperidinyl)-, ethyl ester

HRID 1615405Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8](Cl)=[N:7][CH:6]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[NH2:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.O>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([N:23]2[CH2:24][CH2:25][CH:20]([NH2:19])[CH2:21][CH2:22]2)=[N:7][CH:6]=1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

6-chloronicotinic acid ethyl ester (4.27 g, 23 mmol) was dissolved in DMF (30 ml), and potassium carbonate (4.77 g, 35 mmol) and 4-aminopiperidine (2.76 g, 28 mmol) were added thereto, followed by stirring at 80° C. for 3 hours and at 100° C. for 1 hour. After the reaction mixture was cooled to room temperature, water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated sodium chloride, and then dried over anhydrous sodium sulfate. After the desiccant was filtered off, the solvent was evaporated under reduced pressure, thereby obtaining 6-(4-aminopiperidin-1-yl)nicotinic acid ethyl ester (4.17 g, 73%) as a pale brown oil.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with water and saturated sodium chloride
dry with materialdried over anhydrous sodium sulfate
filtrationAfter the desiccant was filtered off
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-ddb0f9dd208046abb8126469e67ec51d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765750B2

Reaction notes

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