Phenethyl bromide → HCID 13756055, compound

HRID 1763014Notes

Reaction equation

HRID 1763014 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 300ml of dichloromethane and 200 ml of 50% NaOH were combined 10.00 g of 9-amino-3,4-dihydro-acridin-1(2H)-one, 28ml (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 28ml of 2-phenethyl bromide was added at intervals of 12 hours. After 4 days 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 intervals of 12 hours
  2. customAfter 4 days the layers were separated
  3. customthe dichloromethane layer was evaporated to an oil, which
  4. extractionwas extracted into 3N HCl
  5. washwashed with EtOAc
  6. extractionThe resulting precipitate was extracted into dichloromethane
  7. customthe dichloromethane layer was evaporated to an oil
  8. additioncontaining mostly the starting material
  9. customThe purification method
  10. customThe product thus obtained
  11. customwas recrystallized from dichloromethane/hexanes

Sources & evidence

ORD record
ord-319e8effd37740189503202bb59b8d50
Source dataset
uspto-grants-1989_05
Patent number
US04835275

Reaction notes

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