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

HRID 1183076Notes

Reaction equation

HRID 1183076 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 104%

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, 0.66 mmol), and stirred at room temperature overnight. A 2N-hydrogen chloride methanol solution (0.5 ml) was added to the mixture, and stirred at 50° C. for 3 hours. Triethylamine (0.64 ml) was then added to the reaction mixture, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (dichloromethane). The purified product was concentrated under reduced pressure to thereby obtain 186.3 mg (yield: quantitative) of 3-[(2-pyridin-3-ylethyl)pyridin-4-ylmethylamino]propan-1-ol as an orange oil.

Workup

  1. stirringstirred at 50° C. for 3 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by basic silica gel column chromatography (dichloromethane)
  4. concentrationThe purified product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1f873d8bd3524e05b6835abaeef669e6
Source dataset
uspto-grants-2014_03
Patent number
US08664217B2

Reaction notes

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