Water → N-(3-Nitrobenzyl)-2-phenylethanamine

HRID 1861952Notes

Reaction equation

HRID 1861952 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][NH:11][CH3:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(N(CC)CC)C.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>C(#N)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][NH:11][CH2:12][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 8471TriethylamineHCID 409439N-methyl-1-(3-nitrophenyl)methanamine

Product 1

HCID 596729N-(3-Nitrobenzyl)-2-phenylethanamineYield 95.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the compound (630 mg) obtained in Example 42 and triethylamine (768 mg) in acetonitrile (20 ml), benzyl bromide (778 mg) was added dropwise at room temperature. The reaction mixture was stirred at room temperature for 1 h and, after addition of water, extracted with ethyl acetate. The organic layer was washed with 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, n-hexane:ethyl acetate=4:1) to give 925 mg of the titled compound (yield, 95%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-2480925f023a469e920dd2938fecb6f2
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

Loading…