Water → HCID 23014682, compound

HRID 15704Notes

Reaction equation

HRID 15704 reaction equation
[CH:1]1([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH:12]=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[BH4-].[Na+].O>C(O)C.C1(C)C=CC=CC=1>[CH:1]1([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH2:12][NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 6115AnilineHCID 4311764Sodium borohydrideHCID 130234882-(1-Indenyl)benzaldehyde

Product 1

HCID 23014682HCID 23014682, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

To a solution of 2-(1-indenyl)benzaldehyde (7.0 mmol) in ethanol (19.4 mL) was added dropwise aniline (7.3 mmol) under a nitrogen atmosphere. The mixture was stirred at room temperature. After disappearance of the aldehyde was confirmed by gas chromatography, The solvent was distilled off under reduced pressure. After addition of ethanol (19.4 mL), sodium borohydride (4.5 mmol) was added to the solution and the mixture was reacted at room temperature for 3 hrs. Water and toluene were then added to the reaction mixture. The organic layer was dried and concentrated. The obtained oily substance was purified by silica gel column chromatography to give N-[2-(1-indenyl)phenylmethyl]-N-phenylamine (1.48 g, yield 24.0%) as a yellow oily substance.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionwas added to the solution
  3. customthe mixture was reacted at room temperature for 3 hrs
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customThe obtained oily substance was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e7450ae0d3dd42d2955cb45fe1c4c29e
Source dataset
uspto-grants-2010_06
Patent number
US07732643B2

Reaction notes

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