Benzaldehyde → 2-(phenyl-N-(2-methoxyphenyl)aminomethyl)cyclohexanone

HRID 539495

Reaction equation

HRID 539495 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[C:12]([NH2:17])=[CH:13][CH:14]=[CH:15][CH:16]=1.[C:18]1([O:24][Si](C)(C)C)[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1>[Sc].O>[C:2]1([CH:1]([NH:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH3:9])[CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][C:18]2=[O:24])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 70002-MethoxyanilineHCID 81161Cyclohexene, 1-((trimethylsilyl)oxy)-

Product 1

HCID 40533912-(phenyl-N-(2-methoxyphenyl)aminomethyl)cyclohexanoneYield 92%

Reagents, catalysts & solvents 2

HCID 23952ScandiumCatalystHCID 962WaterSolvent

Procedure

Water (0.25 ml) was added to the silica gel supporting scandium produced in Example 1 (75 mg), and while stirring, benzaldehyde (0.125 mmol) and o-anisidine (0.125 mmol) and 1-cyclohexenyloxytrimethylsilane (0.25 mmol) were continuously added. The mixture was stirred at room temperature for 24 hours. The mixture was extracted four times by a decantation method using a mixture of ethyl acetate-hexane (1:1), the solvent was distilled off under reduced pressure, and then the residue was purified by silica gel thin layer chromatography, to obtain the target product, 2-(phenyl-N-(2-methoxyphenyl)aminomethyl)cyclohexanone at a syn/anti ratio of 53/47. Yield 92%.

Workup

  1. stirringThe mixture was stirred at room temperature for 24 hours
  2. extractionThe mixture was extracted four times by a decantation method
  3. additiona mixture of ethyl acetate-hexane (1:1)
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel thin layer chromatography

Sources & evidence

ORD record
ord-669339a405e549c3aa8781a15167b649
Source dataset
uspto-grants-2014_10
Patent number
US08871668B2

Linked notes

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