4-Piperidinecarboxylic acid → 1-(5-Cyano-2-pyridinyl)-4-piperidinecarboxylic acid

HRID 1756996Notes

Reaction equation

HRID 1756996 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+:17].[CH3:18][N:19]([CH3:22])C=O>O>[C:7]([CH:4]1[CH2:5][CH2:6][N:1]([C:18]2[CH:2]=[CH:3][C:4]([C:5]#[N:17])=[CH:22][N:19]=2)[CH2:2][CH2:3]1)([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 37734-Piperidinecarboxylic acidHCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 25517Ammonium Chloride

Product 1

HCID 162274741-(5-Cyano-2-pyridinyl)-4-piperidinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 1.8 g of 6-bromonicotinic acid nitrile, 1.3 g of 4-piperidinylcarboxylic acid and 1.06 g of sodium carbonate in 15 ml of dimethylformamide is stirred for 2 hours at 120° C. After cooling, the suspension is diluted with water. 2.0 g of ammonium chloride are added and the aqueous phase is extracted with ethyl acetate. The organic phase is washed with saturated saline solution, dried over sodium sulphate and the solvent is removed under reduced pressure. Yield: 1.2 g (52% of theory), Rf value: 0.29 (silica gel; methylene chloride/methanol/conc. ammonia=4:1:0.25)

Workup

  1. temperatureAfter cooling
  2. extractionthe aqueous phase is extracted with ethyl acetate
  3. washThe organic phase is washed with saturated saline solution
  4. dry with materialdried over sodium sulphate
  5. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-c8d40d25565e4cb28b86cea43d6456e7
Source dataset
uspto-grants-1995_08
Patent number
US05442064

Reaction notes

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