Ethyl piperazine-1-acetate → HCID 68304438, compound

HRID 1846678Notes

Reaction equation

HRID 1846678 reaction equation
[NH2:1][C:2]1[C:3](Cl)=[N:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1.[CH2:13]([O:15][C:16](=[O:24])[CH2:17]N1CCNCC1)[CH3:14]>O>[CH2:13]([O:15][C:16](=[O:24])[CH2:17][CH:7]1[CH2:6][CH2:5][N:4]([C:3]2[C:2]([NH2:1])=[CH:7][CH:6]=[C:5]([C:8]([F:11])([F:10])[F:9])[N:4]=2)[CH2:3][CH2:2]1)[CH3:14]

Participants

4

Reactant 2

HCID 207112Ethyl piperazine-1-acetateHCID 27376462-Chloro-6-(trifluoromethyl)pyridin-3-amine

Product 1

HCID 68304438HCID 68304438, compoundYield 154.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A neat mixture of 0.500 g (2.54 mmol) of 3-amino-2-chloro-6-trifluoromethylpyridine and 0.870 g (5.09 mmol) of piperazin-1-yl-acetic acid ethyl ester is heated to 150° C. and stirred for 20 h. The mixture is cooled to room temperature, diluted with water, and extracted with ethyl acetate. The combined organic layer is washed with water followed by brine and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude material is purified by flash silica gel chromatography to provide 0.650 g (77.1%) of (3′-amino-6′-trifluoromethyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-acetic acid ethyl ester as a brown oil.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material is purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-efe88f1039f848ef91246bd653cae8c2
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

Loading…