Benzyl Bromide → N,N-dibenzyl-7-methoxynaphthalen-1-amine

HRID 1675487Notes

Reaction equation

HRID 1675487 reaction equation
C1([C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]([N:14]=[C:15]=S)=[CH:6][CH:5]=2)CC1.[C:17](=[O:20])([O-])[O-].[K+].[K+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(O[CH2:35][CH3:36])(=O)C>CC(C)=O>[CH2:23]([N:14]([CH2:15][C:36]1[CH:35]=[CH:6][CH:5]=[CH:4][CH:13]=1)[C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:20][CH3:17])[CH:9]=2)[CH:4]=[CH:5][CH:6]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 565954581-Cyclopropyl-4-isothiocyanatonaphthalene

Product 1

HCID 59813090N,N-dibenzyl-7-methoxynaphthalen-1-amineYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred mixture of 3 (6.94 g, 40 mmol) and potassium carbonate (16.6 g, 120 mmol) in acetone (100 mL) was added benzyl bromide (19.0 mL, 160 mmol) at 0° C. The mixture was refluxed for 3 days and cooled to room temperature. The precipitate removed and the filtrate concentrated. The resulting residue was purified by column chromatography (Hex 100%) to remove the unreacted benzyl bromide and then with ethyl acetate (100%) to give 11.75 g, 83% yield of N,N-dibenzyl-7-methoxynaphthalen-1-amine (4).

Workup

  1. temperatureThe mixture was refluxed for 3 days
  2. customThe precipitate removed
  3. concentrationthe filtrate concentrated
  4. customThe resulting residue was purified by column chromatography (Hex 100%)
  5. customto remove the unreacted benzyl bromide

Sources & evidence

ORD record
ord-0a9c9921f3db4806a0e4f0d026c376e2
Source dataset
uspto-grants-2011_08
Patent number
US08003681B2

Reaction notes

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