Water → N-(2-Hydroxyethyl)-N-[[2-(3,4,5-trimethoxyphenyl)-pyridin-4-yl]methyl]amine

HRID 2303355Notes

Reaction equation

HRID 2303355 reaction equation
C[O:2][C:3](=O)[CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=2)[CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[OH:2][CH2:3][CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 18460587N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]glycine methyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 18460604N-(2-Hydroxyethyl)-N-[[2-(3,4,5-trimethoxyphenyl)-pyridin-4-yl]methyl]amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[[2-(3,4,5-Trimethoxyphenyl)pyridin-4-yl]methyl]-glycine methyl ester (6.54 g) was dissolved in THF (80 mL), and to the solution lithium aluminum hydride (717 mg) was gradually added portionwise at 0° C. under an argon atmosphere, and the mixture was stirred for 4 hours. A small amount of water was added to the reaction mixture. When bubbling ended, sodium sulfate was excessively added. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (chloroform:methanol=20:1) to obtain the title compound.

Workup

  1. customWhen bubbling
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-e776f0ecddd4432cb997ae7b336cc854
Source dataset
uspto-grants-2002_08
Patent number
US06432957B1

Reaction notes

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