Sodium borohydride → 1-(4-Ethylpiperazin-1-yl)-3-(2-hydroxy-2-phenylethyl)isoquinoline

HRID 1814587Notes

Reaction equation

HRID 1814587 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([CH2:19][C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:21])[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([N:3]1[CH2:4][CH2:5][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([CH2:19][CH:20]([OH:21])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:10]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 225034511-(4-Ethylpiperazin-1-yl)-3-phenacylisoquinoline

Product 1

HCID 225032721-(4-Ethylpiperazin-1-yl)-3-(2-hydroxy-2-phenylethyl)isoquinolineYield 87.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the resulting 1-(4-ethylpiperazin-1-yl)-3-phenacylisoquinoline (0.92 g) in methanol (30 ml) was added sodium borohydride (0.12 g) at room temperature. One hr later, the reaction mixture was concentrated. The resulting residue was partitioned between ethyl acetate and water, and extracted with ethyl acetate. The resulting organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was removed, to give the title compound (0.81 g) as a pale yellow oil.

Workup

  1. concentrationOne hr later, the reaction mixture was concentrated
  2. customThe resulting residue was partitioned between ethyl acetate and water
  3. extractionextracted with ethyl acetate
  4. washThe resulting organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-5441f997168b4e71b2bf33e172cbce7f
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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