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

HRID 1504167Notes

Reaction equation

HRID 1504167 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-63cfd05b3d2a438aa3ea1b4bc8778b70
Source dataset
uspto-grants-2015_12
Patent number
US09212187B2

Reaction notes

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