Water → N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethyl]-N-phenylamine

HRID 15702Notes

Reaction equation

HRID 15702 reaction equation
[CH3:1][C:2]1[CH:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH:16]=[N:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7].[BH4-].[Na+].O.C1(C)C=CC=CC=1>C(O)C>[CH3:1][C:2]1[CH:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 4311764Sodium borohydrideHCID 131727117N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethylene]-N-phenylamine

Product 1

HCID 131727118N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethyl]-N-phenylamineYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethylene]-N-phenylamine (3.0 mmol) in ethanol (9.0 ml) was added sodium borohydride (4.5 mmol) and the mixture was reacted at room temperature for 3 hrs. Water and toluene were then added to the mixture. The organic layer was dried and concentrated. The obtained oily substance was purified by silica gel column chromatography to give N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethyl]-N-phenylamine (0.60 g, yield 66.0%) as a yellow oily substance.

Workup

  1. customthe mixture was reacted at room temperature for 3 hrs
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customThe obtained oily substance was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-14488c8cccba42ee9fe93d7646c41e3b
Source dataset
uspto-grants-2010_06
Patent number
US07732643B2

Reaction notes

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