2-Bromoethanol → HCID 54258687, compound

HRID 981912Notes

Reaction equation

HRID 981912 reaction equation
[CH2:1]([NH:8][C:9]1[C:10]2[C:15]([N:16]=[C:17]3[C:22]=1[CH:21]([OH:23])[CH2:20][CH2:19][CH2:18]3)=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[Br:29][CH2:30][CH2:31]O>FC(F)(F)C(O)=O>[CH2:1]([NH:8][C:9]1[C:10]2[C:15]([N:16]=[C:17]3[C:22]=1[CH:21]([O:23][CH2:31][CH2:30][Br:29])[CH2:20][CH2:19][CH2:18]3)=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 60601SuronacrineHCID 516892Sodium Bicarbonate

Product 1

HCID 54258687HCID 54258687, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidCatalyst

Procedure

To a suspension of 9-benzylamino-1,2,3,4-tetrahydroacridin-1ol (7.20 g) in 2-bromoethanol (45 ml) was added 40 drops of trifluoroacetic acid. The reaction mixture was stirred at ambient temperature for 20 mins, added to iced sodium bicarbonate solution, and the suspension 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→1% triethylamine/ethyl acetate) to give 6.85 g (71%) of product. Recrystallization from cyclohexane gave the analytical sample, mp 89°-91° C.

Workup

  1. extractionthe suspension 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→1% triethylamine/ethyl acetate)

Sources & evidence

ORD record
ord-e1a2ddf511e345ad91779ac0a0c6f335
Source dataset
uspto-grants-1991_02
Patent number
US04994452

Reaction notes

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