Triethylamine → N-(5-acenaphthyl)-4-tert-butylbenzylamine

HRID 1006052Notes

Reaction equation

HRID 1006052 reaction equation
[CH2:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[C:6]([NH2:13])=[CH:5][CH:4]=[C:3]3[CH2:2]1.C(N(CC)CC)C.[C:21]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22]>C1(C)C=CC=CC=1>[CH2:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[C:6]([NH:13][CH2:29][C:28]2[CH:31]=[CH:32][C:25]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:26][CH:27]=2)=[CH:5][CH:4]=[C:3]3[CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 625475-AminoacenaphtheneHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzene

Product 1

HCID 15480727N-(5-acenaphthyl)-4-tert-butylbenzylamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
4 °C

Procedure

A mixture of 5-acenaphthylamine (1.0 g, 6 mmol) and triethylamine (0.76 g, 7.5 mmol) in toluene (50 mL) was stirred at 4° C., and 4-tert-butylbenzyl-bromide (1.36 g, 6 mmol) was added in slowly. The reaction mixture was stirred at 23° C. for 15 hours and precipitates formed. The precipitates (triethylamine.HBr) were filtered out; the filtrate was concentrated to dryness. Then the crude reaction mixture was purified by column chromatography (SiO2, hexane/CH2Cl2=5/1). N-(5-acenaphthyl)-4-tert-butylbenzylamine (1.67 g, an oil) was obtained.

Workup

  1. stirringThe reaction mixture was stirred at 23° C. for 15 hours
  2. customprecipitates
  3. customformed
  4. customThe precipitates (triethylamine.HBr)
  5. filtrationwere filtered out
  6. concentrationthe filtrate was concentrated to dryness
  7. customThen the crude reaction mixture
  8. customwas purified by column chromatography (SiO2, hexane/CH2Cl2=5/1)

Sources & evidence

ORD record
ord-3bf4d2f04cad4df289538929237976eb
Source dataset
uspto-grants-2004_09
Patent number
US06787569B1

Reaction notes

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