Benzaldehyde → N-benzyl-N-[2-(9H-carbazol-2-yloxy)]ethylamine

HRID 2299561Notes

Reaction equation

HRID 2299561 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:9]1[C:21]2[NH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]=2[CH:12]=[CH:11][C:10]=1[O:22][CH2:23][CH2:24][NH2:25]>CO.[Pt]=O>[CH2:1]([NH:25][CH2:24][CH2:23][O:22][C:10]1[CH:11]=[CH:12][C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:20][C:21]=2[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 240Benzaldehyde2×HCID 110854932-(9H-carbazol-2-yloxy)ethylamine

Product 1

HCID 11267065N-benzyl-N-[2-(9H-carbazol-2-yloxy)]ethylamine

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

Benzaldehyde (9.38 g) was added to a solution of N-[2-(9H-carbazol-2-yloxy)]ethylamine (20 g; synthesized according to the process indicated in JP-A-9-249623) in methanol (500 mL). The mixture was then stirred at room temperature for 1 hour. Under an argon atmosphere, platinum oxide (1.00 g; mfd. by Wako Pure Chemical Industries) was added to the mixture, which was then stirred under a hydrogen atmosphere at atmospheric pressure for 3 hours. After replacing the atmosphere in the reaction system with argon, benzaldehyde (1.88 g) was added to the mixture, which was then further stirred under a hydrogen atmosphere at atmospheric pressure for 3 hours. After replacing the atmosphere with argon, the catalyst was filtered off and the solvent was distilled off under reduced pressure. The residue was recrystallized from ethanol and dried under reduced pressure to give the title compound (25.2 g) as a pale yellow crystal.

Workup

  1. customsynthesized
  2. stirringwas then stirred under a hydrogen atmosphere at atmospheric pressure for 3 hours
  3. additionwas added to the mixture, which
  4. stirringwas then further stirred under a hydrogen atmosphere at atmospheric pressure for 3 hours
  5. filtrationthe catalyst was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was recrystallized from ethanol
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-84ede2cca9b7401c9fd33d743064dcf9
Source dataset
uspto-grants-2002_12
Patent number
US06495701B1

Reaction notes

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