p-Toluenesulfonic acid → HCID 18784134, compound

HRID 1108767Notes

Reaction equation

HRID 1108767 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:13][CH2:12][C:11](=O)[CH2:10]2)=[CH:5][CH:4]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:15]([NH:22][CH:11]1[CH2:12][CH2:13][CH:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:10]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7504BenzylamineHCID 140909103-(4-Methoxyphenyl)cyclopentan-1-one

Product 1

HCID 18784134HCID 18784134, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-(4-Methoxyphenyl) cyclopentanone (7.37 g) and benzylamine (4.15 g) were refluxed for 1.25 hours in benzene (150 ml) in the presence of p-toluenesulfonic acid (820 mg) using a Dean-Stark apparatus while removing the water generated. After distilling off the benzene under reduced pressure, it was dissolved in methanol (150 ml) while cooling on ice, sodium borohydride (1.63 g) was gradually added and the mixture was stirred at room temperature for 12.5 hours. After concentrating the reaction solution, water was added, and extraction with chloroform was followed by washing with saturated sodium bicarbonate water and saturated saline. After drying with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to produce a light yellow oily substance which was then purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to give 10.0 g of N-benzyl-N-[3-(4-methoxyphenyl)cyclopentyl]amine (91.7% yield).

Workup

  1. customwhile removing the water
  2. distillationAfter distilling off the benzene under reduced pressure, it
  3. dissolutionwas dissolved in methanol (150 ml)
  4. temperaturewhile cooling on ice, sodium borohydride (1.63 g)
  5. additionwas gradually added
  6. concentrationAfter concentrating the reaction solution, water
  7. additionwas added
  8. extractionextraction with chloroform
  9. washby washing with saturated sodium bicarbonate water and saturated saline
  10. dry with materialAfter drying with anhydrous magnesium sulfate
  11. distillationthe solvent was distilled off under reduced pressure
  12. customto produce a light yellow oily substance which
  13. customwas then purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-44c6419fd6b24bbfaadd4b015474cccb
Source dataset
uspto-grants-2000_05
Patent number
US06069176

Reaction notes

Loading…