Potassium Carbonate → HCID 57960268, compound

HRID 1846671Notes

Reaction equation

HRID 1846671 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1F)([O-:3])=[O:2].[CH2:11]([O:13][C:14](=[O:22])[CH2:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH2:11]([O:13][C:14](=[O:22])[CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:18][CH2:17]1)[CH3:12]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 2760465Ethyl 2-(piperidin-4-yl)acetate

Product 1

HCID 57960268HCID 57960268, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.00 g (7.09 mmol) of 2-nitrofluorobenzene in N,N-dimethylformamide (50 mL) is added 1.3 g (7.6 mmol) of 2-(piperdin-4-yl)-acetic acid ethyl ester followed by 1.0 g (7.2 mmol) of potassium carbonate. The mixture is stirred at room temperature for 2 hours. The mixture is diluted with water and washed with ethyl acetate. The combined organic phase is washed with water followed by brine then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography to provide 1.85 g (89%) of [1-(2-nitro-phenyl)-piperidin-4-yl]-acetic acid ethyl ester as an orange oil.

Workup

  1. washwashed with ethyl acetate
  2. washThe combined organic phase is washed with water
  3. dry with materialthen dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-7757c66cca814956ad642148f24f9466
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

Loading…