Phenethyl bromide → HCID 13756055, compound

HRID 1249412Notes

Reaction equation

HRID 1249412 reaction equation
[OH-].[Na+].[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.[CH:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26]Br)=[CH:21][CH:20]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH2:26]([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)[CH2:25][C:22]1[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 7666Phenethyl bromide2×HCID 14798Sodium HydroxideHCID 1843619-amino-3,4-dihydroacridin-1(2H)-one

Product 1

HCID 13756055HCID 13756055, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

In a mixture consisting of 300 ml of dichloromethane and 200 ml of 50% NaOH were combined 10.00 g of 9-amino-3,4-dihydroacridin-1(2H)-one, 28 ml (6 eq) of 2-phenethyl bromide, and 3 g (0.2 eq) of tetrabutylammonium hydrogensulfate catalyst. The mixture was mechanically stirred for 4 days, during which 28 ml of 2-phenethyl bromide was added at intevals of 12 hours. After 4 days the reaction would go no further. The layers were separated and the dichloromethane layer was evaporated to an oil, which was extracted into 3N HCl and washed with EtOAc. The HCl solution was then made basic with 10% NaOH. The resulting precipitate was extracted into dichloromethane and the dichloromethane layer was evaporated to an oil containing mostly the starting material and the end product. The purification method was chromatography on silica gel with 20% EtOAc/dichloromethane solvent. The product thus obtained was recrystallized from dichloromethane/hexanes to yield 2.52 g (17%) of a solid, melting point 129°-132° C.

Workup

  1. additionwas added at intevals of 12 hours
  2. customAfter 4 days the reaction
  3. customThe layers were separated
  4. customthe dichloromethane layer was evaporated to an oil, which
  5. extractionwas extracted into 3N HCl
  6. washwashed with EtOAc
  7. extractionThe resulting precipitate was extracted into dichloromethane
  8. customthe dichloromethane layer was evaporated to an oil
  9. additioncontaining mostly the starting material
  10. customThe purification method
  11. customThe product thus obtained
  12. customwas recrystallized from dichloromethane/hexanes

Sources & evidence

ORD record
ord-b7868104e432479c82d18721cffc976e
Source dataset
uspto-grants-1986_12
Patent number
US04631286

Reaction notes

Loading…