3-(methoxymethyl)pyridine → HCID 14553814, compound

HRID 1904280Notes

Reaction equation

HRID 1904280 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.[O:10]([C:17]1[CH:18]=[C:19]([CH2:23][CH:24]([CH3:27])[CH2:25]I)[CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[O:10]([C:17]1[CH:18]=[C:19]([CH2:23][CH:24]([CH3:27])[CH2:25][N:6]2[CH2:7][CH2:8][CH:9]=[C:4]([CH2:3][O:2][CH3:1])[CH2:5]2)[CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 3389263-(methoxymethyl)pyridineHCID 14553813HCID 14553813, compound

Product 1

HCID 14553814HCID 14553814, compoundYield 20%

Procedure

3-Methoxymethylpyridine (1.75 g) was added to 3-(m-phenoxyphenyl)-2-methylpropyl iodide (1.0 g) at room temperature, and the resultant mixture was stirred at 120° C. for 4 hours. The reaction mixture was cooled to room temperature and washed with diethyl ether three times. Methanol (20 ml) was added thereto, and after addition of sodium borohydride (0.21 g) at room temperature, the resultant mixture was stirred at the same temperature for 15 hours. The resultant mixture was admixed with water (200 ml) and 15% aqueous sodium hydroxide solution (20 ml) and extracted with diethyl ether (50 ml×3). The extracts were combined together, washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to give N-[3-(m-phenoxyphenyl)-2-methylpropyl]-3-methoxymethyl-1,2,5,6-tetrahydropyridine (0.2 g).

Workup

  1. washwashed with diethyl ether three times
  2. additionMethanol (20 ml) was added
  3. additionafter addition of sodium borohydride (0.21 g) at room temperature
  4. extractionextracted with diethyl ether (50 ml×3)
  5. washwashed with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-fba7abe601e343db81cc14b42e686569
Source dataset
uspto-grants-1989_06
Patent number
US04837236

Reaction notes

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