Methanol → HCID 178443397, compound

HRID 2386115Notes

Reaction equation

HRID 2386115 reaction equation
CO.[NH:3]1[CH:7]=[C:6]([CH:8]=O)[N:5]=[CH:4]1.[CH2:10]([NH2:20])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>Cl.[Pd].C(OCC)(=O)C>[CH2:10]([NH:20][CH2:8][C:6]1[N:5]=[CH:4][NH:3][CH:7]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 3

HCID 887MethanolHCID 8916DecylamineHCID 764281H-Imidazole-4-carbaldehyde

Product 1

HCID 178443397HCID 178443397, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 500 mL flask under a nitrogen atmosphere was charged with anhydrous methanol (150 mL), imidazole-4-carboxaldehyde (45.82 grams, 476 mmol) and decylamine (74.99 grams, 476 mmol) with stirring. Several drops of concentrated hydrochloric acid were added to the mixture and the mixture was allowed to reflux overnight under nitrogen. The mixture was taken up into ethyl acetate, washed with water and brine, dried with sodium sulfate, and evaporated to dryness. The crude product was dissolved in a 4:1 ratio of anhydrous THF and anhydrous MeOH and transferred to a hydrogenation reaction flask. To this solution was added 5 wt. % Pd/C (5 wt. %) and the resulting mixture was hydrogenated overnight at 30 psi H2. After hydrogenation was complete, the solution was filtered through Celite under vacuum to remove the Pd/C and the filtrate was evaporated to dryness. 1H NMR (CDCl3) δ 7.5-7.6 (1H), 6.8-6.9 (1H), 3.6-3.8 (2H), 2.6 (t, 2H), 1.5 (t, 2H), 1.2-1.4 (m, 14H), 0.8-0.9 (t, 3H).

Workup

  1. temperatureto reflux overnight under nitrogen
  2. washwashed with water and brine
  3. dry with materialdried with sodium sulfate
  4. customevaporated to dryness
  5. dissolutionThe crude product was dissolved in a 4:1 ratio of anhydrous THF and anhydrous MeOH
  6. customtransferred to a hydrogenation reaction flask
  7. filtrationthe solution was filtered through Celite under vacuum
  8. customto remove the Pd/C
  9. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-1dad0a5f085b4a85b70914499fb2dd34
Source dataset
uspto-grants-2012_09
Patent number
US08268761B2

Reaction notes

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