Ammonium Chloride → 7-(Diphenylhydroxymethyl)-1-(4-methyl-1-piperazinyl)-naphthalene

HRID 235135Notes

Reaction equation

HRID 235135 reaction equation
[C:1]([C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2[N:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]1([Mg]Br)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[Cl-].[NH4+]>C1COCC1>[C:2]1([C:1]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([OH:8])[C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][CH:15]=[C:16]3[N:19]3[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]3)=[CH:11][CH:10]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 189675207-Benzoyl-1-(4-methyl-1-piperazinyl)naphthaleneHCID 178418255HCID 178418255, compound2×

Product 1

HCID 233534897-(Diphenylhydroxymethyl)-1-(4-methyl-1-piperazinyl)-naphthaleneYield 92.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The title product of example 43 (0.072 g, 0.218 mmol) was dissolved in dry THF (10 mL) and chilled to 0° C. Phenyl magnesium bromide (3 M in ether, 0.08 mL, 0.24 mmol) was added dropwise. The mixture turned greenish and then returned to a yellow color. The reaction was allowed to warm to room temperature for 30 minutes and then refluxed for 45 minutes. Additional phenyl magnesium bromide (0.1 mL, 0.26 mmol) was added and the mixture was refluxed 1 hour more. Saturated aqueous ammonium chloride was added and the mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate and concentrated to a light yellow oil. The product was purified by silica gel flash chromatography (1×6 inches). Elution with 50% ethyl acetate/hexane followed by ethyl acetate gave 0.082 g (92%) of the title product. A sample was recrystallized from chloroform/ether for analysis: mp 217.5°-218.5° C. Analysis calculated for C28H28N2O·0.5 H2P: C, 80.54; H, 7.00; N, 6.71. Found: C, 80.47; H, 6.63; N, 6.78.

Workup

  1. temperatureto warm to room temperature for 30 minutes
  2. temperaturerefluxed for 45 minutes
  3. temperaturethe mixture was refluxed 1 hour more
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to a light yellow oil
  8. customThe product was purified by silica gel flash chromatography (1×6 inches)
  9. washElution with 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-9b01cbf13cf24a8f9e39dda70f895ad9
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

Loading…