Piperidine → Methyl 2-chloro-6-(piperidin-1-yl)isonicotinate

HRID 1530206Notes

Reaction equation

HRID 1530206 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:12])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[N:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 93237Methyl 2,6-dichloroisonicotinate

Product 1

HCID 75365494Methyl 2-chloro-6-(piperidin-1-yl)isonicotinateYield 99.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of methyl 2,6-dichloroisonicotinate (1 g, 4.85 mmol), piperidine (0.61 g, 7.28 mmol), K2CO3 (1.38 g, 9.7 mmol) in acetonitrile (20 mL) was heated at 90° C. for 20 h. After completion of reaction, reaction mass was filtered, filtrate concentrated and purified by column to obtain pure methyl 2-chloro-6-(piperidin-1-yl)isonicotinate (1.23 g, 90%).

Workup

  1. customAfter completion of reaction, reaction mass
  2. filtrationwas filtered
  3. concentrationfiltrate concentrated
  4. custompurified by column

Sources & evidence

ORD record
ord-8778ef7f8b3f4e539387a7fefce34d1f
Source dataset
uspto-grants-2015_07
Patent number
US09090562B2

Reaction notes

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