Methanol → HCID 13986696, compound

HRID 329437Notes

Reaction equation

HRID 329437 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10](=O)[CH2:11][CH2:12][CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.B.CO>O1CCCC1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6331Borane2×HCID 13986695HCID 13986695, compound

Product 1

HCID 13986696HCID 13986696, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 13.9 g of N-(2,6-dimethylphenyl)-3-pyridinebutanamide in dry tetrahydrofuran was added dropwise with stirring to an excess of 1 molar borane in tetrahydrofuran and the resulting solution was heated to reflux for two hours. After cooling, excess methanol was added to decompose the remaining borane and the solution was evaporated to dryness. The residue was acidified by the cautious addition of 2N hydrochloric acid and was warmed on the steam bath for 20 minutes. The resulting solution was cooled, made strongly basic with sodium hydroxide solution and was extracted with dichloromethane. The combined layers were dried with potassium carbonate and concentrated to give N-(2,6-dimethylphenyl)-3-pyridine-butanamine as an oil. A solution of the free base in methanol was treated with an excess of fumaric acid in methanol and the resulting solution was diluted with ether. The resulting difumarate was crystallized from 200 ml of 2-propanol to give 20.6 g of N-(2,6-dimethylphenyl) -3-pyridinebutanamine (E)-2-butenedioate(1:2) salt, mp 138°-140° C. (decomposition). Recrystallization from 2-propanol gave the analytical sample, mp 140°-142° C. (decomposition).

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureto reflux for two hours
  3. temperatureAfter cooling
  4. customthe solution was evaporated to dryness
  5. additionThe residue was acidified by the cautious addition of 2N hydrochloric acid
  6. temperaturewas warmed on the steam bath for 20 minutes
  7. temperatureThe resulting solution was cooled
  8. extractionwas extracted with dichloromethane
  9. dry with materialThe combined layers were dried with potassium carbonate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-5e0d9a843c1849f2aac0d12312d1b858
Source dataset
uspto-grants-1990_01
Patent number
US04891429

Reaction notes

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