Velnacrine → HCID 14536409, compound

HRID 1607875Notes

Reaction equation

HRID 1607875 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.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N:17]1([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)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 3655VelnacrineHCID 31268PyrrolidineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 14536409HCID 14536409, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

9-Amino-1,2,3,4-tetrahydroacridin-1-ol (5.36 g) was refluxed overnight in 250 ml of toluene that contained pyrrolidine (7.10 g) and p-toluenesulfonic acid monohydrate (9.5 g). At the end of this time the reaction mixture was washed with an aqueous K2CO3 solution and then the organic phase was concentrated. The residue obtained in this manner was purified by flash chromatography (5% Et3N, toluene) to give, after recrystallization from benzene/pentane, 2.91 g, m.p. 201°-203°.

Workup

  1. washAt the end of this time the reaction mixture was washed with an aqueous K2CO3 solution
  2. concentrationthe organic phase was concentrated
  3. customThe residue obtained in this manner
  4. customwas purified by flash chromatography (5% Et3N, toluene)
  5. customto give
  6. customafter recrystallization from benzene/pentane, 2.91 g, m.p. 201°-203°

Sources & evidence

ORD record
ord-2ab902e03a1141468279b050720d9e1b
Source dataset
uspto-grants-1989_09
Patent number
US04868177

Reaction notes

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