Sodium borohydride → HCID 22502479, compound

HRID 1814583Notes

Reaction equation

HRID 1814583 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]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[C:24](=[O:28])[CH2:23][CH2:22]4)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].[BH4-].[Na+]>CO>[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]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[CH:24]([OH:28])[CH2:23][CH2:22]4)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20720265HCID 20720265, compound

Product 1

HCID 22502479HCID 22502479, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(4-Ethylpiperazin-1-yl)-3-(1-indanon-5-yl)isoquinoline (0.20 g) obtained in the previous Example was dissolved in methanol (20 ml), followed by the addition of sodium borohydride (0.10 g) at room temperature, and the mixture was reacted for 15 min. The reaction solution was concentrated, and the resulting residue was partitioned between ethyl acetate and water. The ethyl acetate layer was separated, washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give the title compound (0.12 g) as a pale yellow oil.

Workup

  1. customthe mixture was reacted for 15 min
  2. concentrationThe reaction solution was concentrated
  3. customthe resulting residue was partitioned between ethyl acetate and water
  4. customThe ethyl acetate layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-0eddda3442d5499a97713355968269d9
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

Loading…