Potassium Carbonate → HCID 14074785, compound

HRID 620896

Reaction equation

HRID 620896 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[C:5]2[C:10]([CH:11]=[C:12]3[C:17]=1[CH:16]=[CH:15][CH:14]=[CH:13]3)=[CH:9][CH:8]=[CH:7][CH:6]=2.C(=O)([O-])[O-].[K+].[K+].[C:24]([C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=1)([CH3:27])([CH3:26])[CH3:25]>C1(C)C=CC=CC=1>[CH3:1][N:2]([CH2:3][C:4]1[C:5]2[C:10]([CH:11]=[C:12]3[C:17]=1[CH:16]=[CH:15][CH:14]=[CH:13]3)=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:32][C:31]1[CH:34]=[CH:35][C:28]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 1881289-(Methylaminomethyl)anthracene

Product 1

HCID 14074785HCID 14074785, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.2 g (0.01 mole) of N-methyl-9-anthrylmethylamine was dissolved in 40 ml of toluene, and 1.7 g (0.012 mole) of anhydrous potassium carbonate was added. With continued stirring at room temperature, 2.49 g (0.011 mole) of p-t-butylbenzylbromide was added, and the mixture was reacted at 40° to 50° C. for 4 hours. The reaction mixture was mixed with ice water, and distributed. The organic layer was washed with water, and toluene was evaporated. The residue was chromatographed on a silica gel column, and eluted with 4% ethyl acetate/n-hexane. The eluate was concentrated to give 3.3 g (yield 91%) of an oily substance.

Workup

  1. customthe mixture was reacted at 40° to 50° C. for 4 hours
  2. washThe organic layer was washed with water, and toluene
  3. customwas evaporated
  4. customThe residue was chromatographed on a silica gel column
  5. washeluted with 4% ethyl acetate/n-hexane
  6. concentrationThe eluate was concentrated
  7. customto give 3.3 g (yield 91%) of an oily substance

Sources & evidence

ORD record
ord-4a1b33b6058c4fceb0c2d4d4d44455ed
Source dataset
uspto-grants-1989_04
Patent number
US04822822

Linked notes

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