3-Pyridinecarboxaldehyde → 1-(4-Ethylpiperazin-1-yl)-3-[(3-pyridyl)hydroxymethyl]isoquinoline

HRID 1251264Notes

Reaction equation

HRID 1251264 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](Br)[N:10]=2)[CH2:5][CH2:4]1)[CH3:2].[Li]CCCC.[CH:25]([C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)=[O:26]>O1CCCC1.C(OCC)(=O)C>[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]([CH:25]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)[OH:26])[N:10]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 225024471-(1-Ethylpiperazin-4-yl)-3-bromoisoquinolineHCID 178418339Butyllithium

Product 1

HCID 225024871-(4-Ethylpiperazin-1-yl)-3-[(3-pyridyl)hydroxymethyl]isoquinolineYield 35.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(4-ethylpiperazin-1-yl)-3-bromoisoquinoline (0.39 g) obtained in Example 28-2, in tetrahydrofuran (10 ml) was cooled to −78° C., followed by the dropwise addition of 2.5M n-BuLi (0.6 ml). Fifteen minutes later, a solution of 3-formylpyridine (0.2 g) in tetrahydrofuran (3 ml) was added dropwise thereto. The temperature of the reaction solution was gradually raised to room temperature. The reaction solution was diluted with ethyl acetate, washed with brine, water and an aqueous solution of saturated sodium chloride, 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 (0.15 g) as a pale yellow oil.

Workup

  1. washwashed with brine, water
  2. dry with materialan aqueous solution of saturated sodium chloride, and dried over magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-b7cd681e809648ffad9aa957dfdfb594
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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