Potassium Carbonate → (2-Chloro-4-nitrophenyl)-[2-(4-methylpiperidin-1-yl)ethyl]amine

HRID 735115Notes

Reaction equation

HRID 735115 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][NH2:10])[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[Cl:17][C:18]1[CH:19]=[C:20]([N+:25]([O-:27])=[O:26])[CH:21]=[CH:22][C:23]=1F>CN(C=O)C>[Cl:17][C:18]1[CH:19]=[C:20]([N+:25]([O-:27])=[O:26])[CH:21]=[CH:22][C:23]=1[NH:10][CH2:9][CH2:8][N:5]1[CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 7837002-(4-Methylpiperidin-1-yl)ethan-1-amine

Product 1

HCID 55828782(2-Chloro-4-nitrophenyl)-[2-(4-methylpiperidin-1-yl)ethyl]amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 12.02 g (32.45 mmol) of 2-(4-methylpiperidin-1-yl)ethylamine in 100 mL of DMF is combined with 17.94 g (64.82 mmol) of potassium carbonate and stirred for 15 minutes at ambient temperature. Then 5.81 g (32.45 mmol) of 3-chloro-4-fluoronitrobenzene are added and the reaction mixture is stirred for 18 hours. Then the reaction mixture is poured into ice water and the crystalline residue is filtered off. Yield: 8.85 g (91.6% of theory); C14H20ClN3O2 (M=297.78); calc.: molecular ion peak (M+H)+: 298/300; found: molecular ion peak (M+H)+: 298/300.

Workup

  1. stirringthe reaction mixture is stirred for 18 hours
  2. filtrationthe crystalline residue is filtered off

Sources & evidence

ORD record
ord-20512737dc6a41ac897492c3e656c9e2
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

Loading…