Sodium borohydride → 7-(alpha-Hydroxybenzyl)-1-(4-methyl-1-piperazinyl)-naphthalene

HRID 235134Notes

Reaction equation

HRID 235134 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.[BH4-].[Na+]>C(O)C>[OH:8][CH: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)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 189675207-Benzoyl-1-(4-methyl-1-piperazinyl)naphthalene

Product 1

HCID 233535267-(alpha-Hydroxybenzyl)-1-(4-methyl-1-piperazinyl)-naphthaleneYield 0.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title product of example 43 (0.121 g, 0.366 mmol) was dissolved in ethanol (3 mL) and sodium borohydride (0.025 g, 0.66 mmol) was added. The mixture was stirred 1 hour at ambient temperature, then it was concentrated at reduced pressure at 40° C. The residue was partitioned between ethyl acetate and water and the phases were separated. The organic layer was washed with water and brine; then it was dried over magnesium sulfate and concentrated to a light yellow oil. The oil was purified by flash chromatography on silica gel (1×4 inches). Elution with 50% ethyl acetate/hexane removed a fast moving component which was not identified. Continued elution with ethyl acetate gave 0.066 mg of the title product as a light tan oil which solidified. This solid was recrystallized from chloroform/ether to afford 0.033 mg (27%) of the title product as a light tan solid: mp 162.5°-163° C. Analysis calculated for C22H24N2O·0.25 H2O: C, 78.42; H, 7.33; N, 8.31. Found: C, 78.52; H, 7.06; N, 8.31.

Workup

  1. concentrationit was concentrated at reduced pressure at 40° C
  2. customThe residue was partitioned between ethyl acetate and water
  3. customthe phases were separated
  4. washThe organic layer was washed with water and brine
  5. dry with materialthen it was dried over magnesium sulfate
  6. concentrationconcentrated to a light yellow oil
  7. customThe oil was purified by flash chromatography on silica gel (1×4 inches)
  8. washElution with 50% ethyl acetate/hexane
  9. customremoved
  10. washContinued elution with ethyl acetate

Sources & evidence

ORD record
ord-3b9e0ac79c5b4cdc9fc2e0854783ff5f
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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