Water → methyl 6-piperidinonicotinate

HRID 1977279Notes

Reaction equation

HRID 1977279 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][N:9]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[N:1]1([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 11430Potassium CarbonateHCID 254249Methyl 6-chloropyridine-3-carboxylate

Product 1

HCID 2794747methyl 6-piperidinonicotinateYield 86.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of piperidine (2.98 g) and methyl 6-chloronicotinate (5.00 g) in N,N-dimethylformamide (75 ml) was added potassium carbonate (12.08 g). The mixture was stirred at 100° C. for 3 hours. After cooling to ambient temperature, to the reaction mixture was added water (100 ml) and then the mixture was stirred for 15 minutes at ambient temperature. The resulting precipitates were filtered, washed with water, and dried to give methyl 6-(1-piperidyl)nicotinate (5.55 g), as a white solid.

Workup

  1. temperatureAfter cooling to ambient temperature, to the reaction mixture
  2. stirringthe mixture was stirred for 15 minutes at ambient temperature
  3. customThe resulting precipitates
  4. filtrationwere filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-887c41ef35994d05b4ae8608db8e6a85
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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