Velnacrine → HCID 53824737, compound

HRID 1195755Notes

Reaction equation

HRID 1195755 reaction equation
[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH:14](O)[CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.C(=O)(O)[O-].[Na+].[C:22]([O:26][CH3:27])(=[O:25])[CH2:23][SH:24]>S(=O)(=O)(O)O>[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH:14]([S:24][CH2:23][C:22]([O:26][CH3:27])=[O:25])[CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2

Participants

5

Reactant 3

HCID 3655VelnacrineHCID 16907Methyl ThioglycolateHCID 516892Sodium Bicarbonate

Product 1

HCID 53824737HCID 53824737, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a suspension of 9-amino-1,2,3,4-tetrahydroacridin-1-ol (8.82 g) and methyl thioglycolate (40 ml) was added 40 drops of sulfuric acid. The reaction mixture was stirred at ambient temperature for 3 hrs, poured into an iced sodium bicarbonate solution, and extracted with ethyl acetate. The combined organic extracts were washed with water, saturated sodium chloride, and dried over anhydrous magnesium sulfate. The filtrate was concentrated in vacuo and the residue was triturated with ethyl ether to give 2.79 g of product, mp 175°-183°(dec.). Recrystallization from methanol/water gave the analytical sample, mp 194°-196° C. (dec.).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts were washed with water, saturated sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was triturated with ethyl ether

Sources & evidence

ORD record
ord-5f139a096adb4bf59b5979d46f00bc71
Source dataset
uspto-grants-1992_05
Patent number
US05112829

Reaction notes

Loading…