Velnacrine → 1-(2-Bromoethoxy)-1,2,3,4-tetrahydroacridin-9-amine

HRID 981911Notes

Reaction equation

HRID 981911 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH:14]([OH:16])[CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.FC(F)(F)C(O)=O.[OH-].[Na+].[Br:26][CH2:27][CH2:28]O>>[Br:26][CH2:27][CH2:28][O:16][CH:14]1[C:15]2[C:10](=[N:9][C:8]3[C:3]([C:2]=2[NH2:1])=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:11][CH2:12][CH2:13]1

Participants

5

Reactant 4

HCID 3655VelnacrineHCID 6422Trifluoroacetic acidHCID 108982-BromoethanolHCID 14798Sodium Hydroxide

Product 1

HCID 545370311-(2-Bromoethoxy)-1,2,3,4-tetrahydroacridin-9-amineYield 67%

Procedure

To a suspension of 9-amino-1,2,3,4-tetrahydroacridin-1-ol (7.55 g) in 40 ml of 2-bromoethanol was added 9.9 ml of trifluoroacetic acid. The reaction mixture was stirred at ambient temperature for 18 hrs, added to iced sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with water, saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and evaporated. The residue was purified by flash chromatography (ethyl acetate→2% triethylamine/ethyl acetate) to give 7.6 g (67%) of a product. Recrystallization from methanol/water gave the analytical sample, mp 163.5°-164.5° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic extracts were washed with water, saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography (ethyl acetate→2% triethylamine/ethyl acetate)

Sources & evidence

ORD record
ord-ad3492faa3064103ae0c3ab5e552d8da
Source dataset
uspto-grants-1991_02
Patent number
US04994452

Reaction notes

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