Hydrochloric Acid → HCID 14914490, compound

HRID 1861924Notes

Reaction equation

HRID 1861924 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.Cl.[N+:9]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15]N)([O-:11])=[O:10].C([N:22](CC)CC)C.Cl>C(Cl)Cl>[N+:9]([C:12]1[CH:13]=[C:14]([CH2:15][CH2:6][C:5]([NH2:22])=[O:7])[CH:17]=[CH:18][CH:19]=1)([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 2724030Benzenemethanamine, 3-nitro-, hydrochloride (1:1)

Product 1

HCID 14914490HCID 14914490, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (0.08 ml) was added dropwise to a solution of 3-nitrobenzylamine hydrochloride (139 mg) and triethylamine (0.22 ml) in methylene chloride (10 ml) and stirred at room temperature for 2 h. To the reaction mixture, 2 N HCl was added and extraction was performed with methylene chloride; then, the organic layer was washed successively with water and a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate) to give 102 mg of the titled compound (yield, 71%).

Workup

  1. extractionextraction
  2. washthen, the organic layer was washed successively with water
  3. dry with materiala saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-93d9b06042c145c884dd152a9c16fcdd
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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