Triethylamine → 2-(Diphenoxymethyl)pyridine

HRID 2308908Notes

Reaction equation

HRID 2308908 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH:8]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[H][H]>C(O)C.[Pd]>[O:16]([CH:8]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6]1[CH:5]=[CH:4][CH:3]=[CH:2][N:7]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 12833242HCID 12833242, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 136727362-(Diphenoxymethyl)pyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 10.42 grams (g) (0.032 mole (m)) of 6-chloro-2-(diphenoxymethyl)pyridine, 8.02 g (0.079 m) of triethylamine in 200 milliliters (ml) of absolute ethanol in a Parr shaker bottle was added 0.5 g of 5 percent palladium on charcoal. Hydrogen was passed over the liquid surface using a Parr hydrogenator until ~3 pounds (0.3 m) had been consumed. The reaction mixture was filtered and the solvent removed by evaporation under reduced pressure. The residue was poured into a solution of 50 ml of water and 50 ml of 10 percent sodium hydroxide. This solution was extracted with methylene chloride. The extract was washed with water, dried over magnesium sulfate and the solvent stripped away from vacuum. The residue was heated at 0.02 millimeters of mercury to 110° C. to remove lower boiling impurities. The above named product was recovered as a pale yellow oil in a yield of 6.8 g and was ~99 percent pure. The Nuclear Magnetic Resonance spectrum (NMR) confirmed the product. The product has a refractive index of n25/d=1.5946 and upon analysis was found to have carbon, hydrogen and nitrogen contents of 77.78, 5.56 and 4.92 percent, respectively, as compared with the theoretical contents of 77.98, 5.24 and 5.05 percent, respectively, as calculated for the above named compound (Compound 1).

Workup

  1. customhad been consumed
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent removed by evaporation under reduced pressure
  4. additionThe residue was poured into a solution of 50 ml of water and 50 ml of 10 percent sodium hydroxide
  5. extractionThis solution was extracted with methylene chloride
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. temperatureThe residue was heated at 0.02 millimeters of mercury to 110° C.
  9. customto remove lower boiling impurities
  10. customwas recovered as a pale yellow oil in a yield of 6.8 g

Sources & evidence

ORD record
ord-2ab97b2e94064c36a956e8887d33049c
Source dataset
uspto-grants-1987_09
Patent number
US04692183

Reaction notes

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