Potassium Hydroxide → HCID 13935131, compound

HRID 1763022Notes

Reaction equation

HRID 1763022 reaction equation
[OH-].[K+].[NH2:3][C:4]1[C:5]2[C:10]([N:11]=[C:12]3[C:17]=1[C:16](=[O:18])[CH2:15][CH2:14][CH2:13]3)=[CH:9][CH:8]=[CH:7][CH:6]=2.[F:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23]Br>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[F:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][NH:3][C:4]1[C:5]2[C:10]([N:11]=[C:12]3[C:17]=1[C:16](=[O:18])[CH2:15][CH2:14][CH2:13]3)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 680073-Fluorobenzyl bromideHCID 1843619-amino-3,4-dihydroacridin-1(2H)-one

Product 1

HCID 13935131HCID 13935131, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent2×

Procedure

In 300 ml of toluene and 200 ml of 30% potassium hydroxide were combined 8.00 g of 9-amino-3,4-dihydroacridin-1(2H)-one and 1.92 g of tetrabutylammonium hydrogen sulfate catalyst. The mechanically stirred mixture was heated to reflux and a solution of 9.25 ml of 3-fluorobenzyl bromide in 40 ml of toluene was added over 0.5 hour. Then the reaction was further refluxed for 2 hours. The reaction mixture was then poured into 500 ml of ice and the layers were separated. The aqueous layer was extracted with ethyl acetate. The organics were combined and washed with saturated NaCl solution, dried over magnesium sulfate, filtered and evaporated to a solid. The solid was purified by preparative HPLC (ethyl acetate). The product-containing fractions were combined and concentrated to a solid. The solid was recrystallized from 1:1 dichloromethane/pentane to yield 7.15 g of solid, mp 156°-157° C.

Workup

  1. temperatureThe mechanically stirred mixture was heated
  2. temperatureto reflux
  3. temperatureThen the reaction was further refluxed for 2 hours
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washwashed with saturated NaCl solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to a solid
  10. customThe solid was purified by preparative HPLC (ethyl acetate)
  11. concentrationconcentrated to a solid
  12. customThe solid was recrystallized from 1:1 dichloromethane/pentane

Sources & evidence

ORD record
ord-dad5c17212734f45851a6f80534a6dc7
Source dataset
uspto-grants-1989_05
Patent number
US04835275

Reaction notes

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