Chloroform → HCID 69596373, compound

HRID 1793875Notes

Reaction equation

HRID 1793875 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].C(N(C(C)C)CC)(C)C.C(Cl)(Cl)Cl>CN(C=O)C.O>[N+:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][N:4]1[CH2:3][CH2:2][NH2:1])([O-:19])=[O:18]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 33944N-(2-Aminoethyl)piperidineHCID 738951-Fluoro-2-nitrobenzeneHCID 81531Diisopropylethylamine

Product 1

HCID 69596373HCID 69596373, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2-aminoethyl)piperidine (10.0 g, 78.0 mmol) and 2-fluoro-1-nitrobenzene (22.0 g, 156.0 mmol) in DMF (250 mL) was added diisopropylethylamine (12.5 mL) and the mixture was stirred at room temperature for 15 hours. The reaction mixture was poured into a mixture of CHCl3 and water. The water layer was extracted with CHCl3 and the combined organic layers were washed with water and brine, dried (Na2SO4), and evaporated, and the residue was purified by silica gel column chromatography to give 1 (17.6 g, 91%) as a yellowish solid.

Workup

  1. extractionThe water layer was extracted with CHCl3
  2. washthe combined organic layers were washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-731a1441033a4bbc940943dc6dd36e70
Source dataset
uspto-grants-2006_04
Patent number
US07022714B2

Reaction notes

Loading…