3-(methoxymethyl)pyridine → HCID 14553815, compound

HRID 1904282Notes

Reaction equation

HRID 1904282 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][CH:15]([CH3:18])[CH2:16]I)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][CH2:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1>>[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][CH:15]([CH3:18])[CH2:16][N:24]2[CH2:25][CH2:26][CH2:27][CH:22]([CH2:21][O:20][CH3:19])[CH2:23]2)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

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

Product 1

HCID 14553815HCID 14553815, compoundYield 19.9%

Procedure

3-(m-Phenoxyphenyl)-2-methylpropyl iodide (1.0 g) was added to 3-methoxymethylpyridine (1.75 g) at room temperature, and the resultant mixture was stirred at 120° C. for 4 hours, cooled to room temperature and washed with diethyl ether three times. The resultant mixture was admixed with methanol (20 ml) and then with acetic acid (2 ml). To the resulting mixture, 5% palladium-carbon (0.5 g) was added at room temperature under nitrogen stream, and then hydrogenation was carried out under nitrogen stream. After absorption of hydrogen was completed, the catalyst was removed by filtration, and the filtrate was combined with 15% aqueous sodium hydroxide solution (50 ml) and extracted with diethyl ether. The ether layer was 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-methoxymethylpiperidine (0.2 g).

Workup

  1. washwashed with diethyl ether three times
  2. additionTo the resulting mixture, 5% palladium-carbon (0.5 g) was added at room temperature under nitrogen stream
  3. customAfter absorption of hydrogen
  4. customthe catalyst was removed by filtration
  5. extractionextracted with diethyl ether
  6. washThe ether layer was washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d502f630de734596954006e12d877d1a
Source dataset
uspto-grants-1989_06
Patent number
US04837236

Reaction notes

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