Tert-Butylamine → N-(1,1-Dimethylethyl)benzenamine

HRID 1272560Notes

Reaction equation

HRID 1272560 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.Br[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[C:12]1([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 7961BromobenzeneHCID 178418339Butyllithium

Product 1

HCID 254260N-(1,1-Dimethylethyl)benzenamineYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

t-Butylamine (2.0 eq.) was stirred in dry THF at r.t. and n-butyllithium (1.2 eq.) was added slowly. The resulting mixture was stirred for 30 min. and then bromobenzene (1.0 eq.) added, refluxed for 4 hr. After work-up, it was purified and separated by a column(silica) to elute with hexane and ethyl acetate (9:1). Yield 50%.

Workup

  1. temperaturerefluxed for 4 hr
  2. customAfter work-up, it was purified
  3. customseparated by a column(silica)
  4. washto elute with hexane and ethyl acetate (9:1)

Sources & evidence

ORD record
ord-c4d87cacfcde4ab2a7037c0d824807ae
Source dataset
uspto-grants-2007_04
Patent number
US07208517B1

Reaction notes

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