7-Hydroxy-1-(4-methyl-1-piperazinyl)-2,3-dihydronaphthalene → 8-(4-Methylpiperazin-1-yl)naphthalen-2-ol

HRID 235157Notes

Reaction equation

HRID 235157 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([N:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)[CH2:8][CH2:7][CH:6]=2>[Pd].C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 221157307-Hydroxy-1-(4-methyl-1-piperazinyl)-2,3-dihydronaphthalene

Product 1

HCID 108002178-(4-Methylpiperazin-1-yl)naphthalen-2-olYield 34.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

10% Palladium on carbon (1.16 g) and 7-hydroxy-1-(4-methyl-1-piperazinyl)-2,3-dihydronaphthalene (1.48 g, 6.06 mmol) were slurried in toluene (100 mL) and refluxed 16.5 h. The mixture was cooled, filtered, and concentrated. The product was purified by flash chromatography on silica gel (1×6 inches). Elution with 50% ethyl acetate/hexane followed by 100% ethyl acetate gave 0.51 g (34%) of the title product as a light pink foam. A sample was recrystallized from ether to give a cream colored solid for analysis: mp 184°-185° C. Analysis calculated for C15H18N2O: C, 74.35; H, 7.49; N, 11.56. Found: C, 74.05; H, 7.03; N, 11.42.

Workup

  1. temperaturerefluxed 16.5 h
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was purified by flash chromatography on silica gel (1×6 inches)
  6. washElution with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-73e1842a70a441038b36b7ae7d2528ce
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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