HCID 17917423, compound → HCID 178506842, compound

HRID 1387664Notes

Reaction equation

HRID 1387664 reaction equation
[CH3:1][N:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]=1.[Li:18]CCCC>CCCCCC>[CH3:1][N:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([Li:18])[CH:4]=1

Participants

4

Reactant 2

HCID 17917423HCID 17917423, compoundHCID 178418339Butyllithium2×

Product 1

HCID 178506842HCID 178506842, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

N-Methyl-N-phenyl-1H-inden-3-amine(6.8g, 30.7 mmol) was dissolved in 100 mL of hexane and 10 12.3 mL of 2.5 M n-BuLi (0.936 eq) was added dropwise via syringe over a 15 minute period. The solution developed a yellow precipitate upon the addition of n-BuLi and the slurry was allowed to stir overnight. After this time the solid was filtered, washed with 50 mL of hexane and allowed to dry in Vacuo overnight to afford the desired anion as a yellow-orange solid (5.83 g, 25.6 mmol) in 89 percent yield based upon the lithio reagent.

Workup

  1. filtrationAfter this time the solid was filtered
  2. washwashed with 50 mL of hexane
  3. customto dry in Vacuo overnight

Sources & evidence

ORD record
ord-bfaf5a6cb1d247838a01f45a49ef9949
Source dataset
uspto-grants-2001_07
Patent number
US06268444B1

Reaction notes

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