2-Methylpiperidine → HCID 16771415, compound

HRID 336259Notes

Reaction equation

HRID 336259 reaction equation
Cl[C:2]1[CH:9]=[CH:8]C(C#N)=[CH:4][N:3]=1.[CH3:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][NH:12]1.[OH-].[K+].[C:19]([O:22]CC)(=[O:21])[CH3:20]>O>[CH3:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][N:12]1[C:2]1[CH:9]=[CH:8][C:20]([C:19]([OH:22])=[O:21])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 79742-MethylpiperidineHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 16771415HCID 16771415, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-chloronicotinonitrile (Maybridge SPB04745; 1.5 g; 10.8 mmol; 1 eq.) and 2-methylpiperidine (25.6 ml; 216.5 mmol; 20 eq.) was stirred at 90° C. for 24 hours. The mixture was diluted with ethyl acetate, washed with water and brine, dried over magnesium sulphate and concentrated in vacuo. To the residue (1.5 g; 7.45 mmol; 1 eq.) in water (90 mL) was added potassium hydroxide (2.09 g; 37.3 mmol; 5 eq.) and the reaction mixture was refluxed for 16 hours. After cooling to room temperature, the precipitate was filtered off and the filtrate acidified to pH 6 with HCl 1M. The precipitate was filtered off and dried to afford the title compound as a beige solid.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated in vacuo
  4. temperaturethe reaction mixture was refluxed for 16 hours
  5. temperatureAfter cooling to room temperature
  6. filtrationthe precipitate was filtered off
  7. filtrationThe precipitate was filtered off
  8. customdried

Sources & evidence

ORD record
ord-4c4c9859c30c4979a20f8ff588207be4
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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