Velnacrine → HCID 14536412, compound

HRID 1607877Notes

Reaction equation

HRID 1607877 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:17]1([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:17]1([CH:23]2[CH2:24][CH2:25][N:26]([CH:14]3[C:15]4[C:10](=[N:9][C:8]5[C:3]([C:2]=4[NH2:1])=[CH:4][CH:5]=[CH:6][CH:7]=5)[CH2:11][CH2:12][CH2:13]3)[CH2:27][CH2:28]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 3655VelnacrineHCID 698734-PhenylpiperidineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 14536412HCID 14536412, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

9-Amino-1,2,3,4-tetrahydroacridin-1-ol (5.36 g) was refluxed for 48 hours in 300 ml of toluene that contained 4-phenylpiperidine (8.06 g) and p-toluenesulfonic acid monohydrate (9.5 g). At the end of this time the reaction mixture was concentrated and the residue purified by flash chromatography (5% Et3N/toluene) to give, after concentration of theproduct-containing fractions and recrystallization from EtOAc/pentane, 3.22g of analytically pure product, m.p. 189°-190°.

Workup

  1. concentrationAt the end of this time the reaction mixture was concentrated
  2. customthe residue purified by flash chromatography (5% Et3N/toluene)
  3. customto give
  4. customafter concentration of theproduct-containing fractions and recrystallization from EtOAc/pentane, 3.22g of analytically pure product, m.p. 189°-190°

Sources & evidence

ORD record
ord-f7d4236aa9994beba94e34761e7ee233
Source dataset
uspto-grants-1989_09
Patent number
US04868177

Reaction notes

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