Tacrine → 1,2,3,4-Tetrahydroacridine

HRID 748641Notes

Reaction equation

HRID 748641 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[C:5](=[C:7](N)[C:8]3[CH2:14][CH2:13][CH2:12][CH2:11][C:9]=3[N:10]=2)[CH:6]=1.BrCCCC(Cl)=O>C(Cl)(Cl)Cl.CN(C)C=O>[CH2:14]1[C:8]2[C:9](=[N:10][C:4]3[C:5]([CH:7]=2)=[CH:6][CH:1]=[CH:2][CH:3]=3)[CH2:11][CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 1935TacrineHCID 702254-Bromobutyryl chloride

Product 1

HCID 1553151,2,3,4-Tetrahydroacridine

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of tacrine (4 g, 20.17 mmoles) in chloroform (50 ml) and N,N-dimethylformamide (15 ml), 4-bromobutyroylchloride (3.5 ml, 30.25 mmoles) is added. The reaction mixture is maintained under stirring at room temperature for 6 hours and then diluted with chloroform and washed with water. The organic phase, anhydrified with sodium sulphate, is evaporated at reduced pressure. The crude product is purged by chromatography on silica gel, eluting with n-hexane/ethyl acetate 8/2 (ratio by volume). 9-[4-bromo)butyroylamino]-1,2,3,4-tetrahydroacridine is obtained.

Workup

  1. temperatureThe reaction mixture is maintained
  2. washwashed with water
  3. customis evaporated at reduced pressure
  4. customThe crude product is purged by chromatography on silica gel
  5. washeluting with n-hexane/ethyl acetate 8/2 (ratio by volume)

Sources & evidence

ORD record
ord-7cb704a7b3024394a2e669e1c73a362d
Source dataset
uspto-grants-2008_07
Patent number
US07399878B2

Reaction notes

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