Diethyl Ether → HCID 14500421, compound

HRID 1762909Notes

Reaction equation

HRID 1762909 reaction equation
Cl.[CH3:2][C:3]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:4]=1[O:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[OH:8].[C:20]([OH:27])(=[O:26])/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24].CCOCC>CO.[Pt]=O>[C:20]([OH:27])(=[O:26])/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24].[CH3:2][C:3]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:4]=1[O:5][CH2:6][CH:7]([CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][NH:10]1)[OH:8]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 444972Fumaric AcidHCID 14500442HCID 14500442, compound

Product 1

HCID 14500421HCID 14500421, compoundYield 52.9%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent3×

Procedure

A solution of α-[(2,4-dimethylphenoxy)methyl]pyridine-2-methanol hydrochloride (10.0 g, 0.0347 mole) in 200 ml of methanol was hydrogenated at room temperature with 1.4 g of platinum oxide for 1/2 hr. The methanol solution was filtered and solvent removed on the rotary evaporator. The resulting material was dissolved in water, made basic with 10% sodium hydroxide and the free base was extracted into methylene chloride. Removal of methylene chloride on the rotary evaporator gave a yellow oil. While standing overnight the oil crystallized to give a white solid (softens 75°-78° C., 78°-90° C. m.p.). The free base was dissolved in methanol and treated with a methanol solution of an equimolar quantity of fumaric acid. A crystalline white solid was obtained by adding ether, and upon recrystallization from methanol-ethyl ether, 5.81 g (52.9%) of crystalline white product was obtained, m.p. 208°-212° C. with decomposition.

Workup

  1. filtrationThe methanol solution was filtered
  2. customsolvent removed on the rotary evaporator
  3. dissolutionThe resulting material was dissolved in water
  4. extractionthe free base was extracted into methylene chloride
  5. customRemoval of methylene chloride
  6. customon the rotary evaporator
  7. customgave a yellow oil
  8. customthe oil crystallized
  9. customto give a white solid (softens 75°-78° C., 78°-90° C. m.p.)
  10. customA crystalline white solid was obtained
  11. customupon recrystallization from methanol-ethyl ether

Sources & evidence

ORD record
ord-4aaa797ff6134008a48b3ac299e0b548
Source dataset
uspto-grants-1989_05
Patent number
US04835164

Reaction notes

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