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

HRID 399453Notes

Reaction equation

HRID 399453 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-982f539963da45dca583168b614e3093
Source dataset
uspto-grants-1998_10
Patent number
US05821245

Reaction notes

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