4-Methoxybenzylamine → 2-[2-(4-Methoxybenzylamino)pyridin-6-yl]ethanol

HRID 583705Notes

Reaction equation

HRID 583705 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][OH:10])[N:3]=1.[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1>CCOC(C)=O.O>[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH:18][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][OH:10])[N:3]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 754524-MethoxybenzylamineHCID 189285562-(6-Chloropyridin-2-yl)ethanol

Product 1

HCID 185183482-[2-(4-Methoxybenzylamino)pyridin-6-yl]ethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Chloropyridine 30-2 (150 mg, 0.95 mmol) and 4-methoxybenzylamine (4 mL, 31 mmol) were combined neat and heated in a sealed tube at 160° for 4 days. After diluting with EtOAc and water the pH was adjusted to 7 phases separated and the organic phase was washed with brine, dried (MgSO4) and concentrated. Flash chromatography (twice on silica, 50% and 40% EtOAc/hexane) provided 30-3 as a yellow semi-solid.

Workup

  1. temperatureheated in a sealed tube at 160° for 4 days
  2. customseparated
  3. washthe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1ce2e5ed8da04346b5eb2c55632577bc
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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