Methanol → 3-[(2-Pyridin-3-ylethyl)pyridin-4-ylmethylamino]propan-1-ol

HRID 68996Notes

Reaction equation

HRID 68996 reaction equation
CO.Cl.CO.[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH2:13][N:14]([CH2:25][C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[CH2:15][CH2:16][CH2:17][O:18]C2CCCCO2)[CH:7]=1>C(N(CC)CC)C>[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH2:13][N:14]([CH2:25][C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[CH2:15][CH2:16][CH2:17][OH:18])[CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 21893726Hydrochloride methanol2×HCID 66960900(2-Pyridin-3-ylethyl)pyridin-4-ylmethyl-[3-(tetrahydropyran-2-yloxy)propyl]amine

Product 1

HCID 669609373-[(2-Pyridin-3-ylethyl)pyridin-4-ylmethylamino]propan-1-olYield 103.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A 2N-hydrogen chloride methanol solution (1.2 ml) was added to a methanol solution (4 ml) of (2-pyridin-3-ylethyl)pyridin-4-ylmethyl-[3-(tetrahydropyran-2-yloxy)propyl]amine (236 mg). The mixture was stirred at room temperature overnight. A 2N-hydrogen chloride methanol solution (0.5 ml) was added thereto, and the mixture was further stirred at 50° C. for 3 hours. Triethylamine (0.64 ml) was added to the reaction mixture, and the mixture was condensed under reduced pressure. The residue was purified by basic silica gel column chromatography (dichloromethane). The purified product was condensed under reduced pressure to give the title compound (186.3 mg) as an orange oily matter.

Workup

  1. stirringthe mixture was further stirred at 50° C. for 3 hours
  2. customcondensed under reduced pressure
  3. customThe residue was purified by basic silica gel column chromatography (dichloromethane)
  4. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-b69f6ab5a3be41fca59b82a379afdf31
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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