Velnacrine → HCID 14536418, compound

HRID 1607880Notes

Reaction equation

HRID 1607880 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.[CH3:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:17][N:18]1[CH2:23][CH2:22][N:21]([CH:14]2[C:15]3[C:10](=[N:9][C:8]4[C:3]([C:2]=3[NH2:1])=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH2:11][CH2:12][CH2:13]2)[CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 3655VelnacrineHCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 14536418HCID 14536418, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

9-Amino-1,2,3,4-tetrahydroacridin-1-ol (5.36 g) was refluxed for 48 h in 300 ml of toluene that contained 1-methylpiperazine (5.06 g) and p-toluenesulfonic acid monohydrate (9.5 g). At the end of this time the reaction mixture was distributed between EtOAc and aqueous K2CO3 and then the combined organic phase was concentrated and the residue purified by flash chromatography (5% Et3N/EtOAc) to give, after concentration of the product-containing fractions and recrystallization from EtOAc, 2.30 g of analytically pure product, m.p. 200°-202°.

Workup

  1. concentrationthe combined organic phase was concentrated
  2. customthe residue purified by flash chromatography (5% Et3N/EtOAc)
  3. customto give
  4. customafter concentration of the product-containing fractions and recrystallization from EtOAc, 2.30 g of analytically pure product, m.p. 200°-202°

Sources & evidence

ORD record
ord-3de3e4b94900407ba1f5f628c1fff9db
Source dataset
uspto-grants-1989_09
Patent number
US04868177

Reaction notes

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