Water → N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethyl]-N-(2,4,6-trimethylphenyl)amine

HRID 2116830Notes

Reaction equation

HRID 2116830 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[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=2[CH3:26])[C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7].[BH4-].[Na+].O.C1(C)C=CC=CC=1>C(O)(=O)C>[CH3:9][C:4]1[CH:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][NH:17][C:18]2[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=2[CH3:26])[C:2]([CH3:1])=[C:6]([CH3:7])[C:5]=1[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 4311764Sodium borohydrideHCID 131727122N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethylene]-N-(2,4,6-trimethylphenyl)amine

Product 1

HCID 131727123N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethyl]-N-(2,4,6-trimethylphenyl)amineYield 79.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of N-[2-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethylene]-N-(2,4, 6-trimethylphenyl)amine (10.0 mmol) in acetic acid (7.0 mL) was added sodium borohydride (13.0 mmol). The mixture was reacted at room temperature for 1 hr. Water and toluene were then added 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-(2,3,4,5-tetramethylcyclopentadienyl)phenylmethyl]-N-(2,4,6-trimethylphenyl)amine (2.74 g, yield 69.5%) as a yellow oily substance.

Workup

  1. customThe mixture was reacted at room temperature for 1 hr
  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-9b4667fb1c2f430eade29a3af1bb2174
Source dataset
uspto-grants-2008_10
Patent number
US07439379B2

Reaction notes

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