Isobutylamine → 2,4-dimethyl-N-(2-methylpropyl)aniline

HRID 1746395

Reaktionsgleichung

Reaktionsgleichung von HRID 1746395
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH3:9].[CH2:10]([NH2:14])[CH:11]([CH3:13])[CH3:12].O1CCCC1>>[CH3:9][C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[NH:14][CH2:10][CH:11]([CH3:13])[CH3:12]

Komponenten

4

Edukt 3

HCID 6558IsobutylamineHCID 8028TetrahydrofuranHCID 5231531-Chloro-2,4-dimethylbenzene

Produkt 1

HCID 284223892,4-dimethyl-N-(2-methylpropyl)anilineAusbeute 96,3 %

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 1-chloro-2,4-dimethylbenzene (1687 mg, 12 mmol), isobutylamine (1755 mg, 24.00 mmol), and Caddick catalyst (140 mg, 0.238 mmol) was treated with lithium hexamethyl disilizide in tetrahydrofuran (1M LHMDS in THF, 15 mL, 15.00 mmol) under nitrogen. The reaction mixture was heated to 70° C. for 45 min in a septum-sealed vessel. The cooled mixture was concentrated in vacuo and the residue was partitioned between aqueous citric acid (50 mL) and tert butyl methyl ether (TBME) (2×50 mL). The organic phase was treated with dried MgSO4, the solid removed by filtration and the organic phase was concentrated in vacuo to give (2,4-dimethylphenyl)(2-methylpropyl)amine (2.05 g, 11.56 mmol, 96% yield) as an orange oil.

Aufarbeitung

  1. concentrationThe cooled mixture was concentrated in vacuo
  2. customthe residue was partitioned between aqueous citric acid (50 mL) and tert butyl methyl ether (TBME) (2×50 mL)
  3. additionThe organic phase was treated with dried MgSO4
  4. customthe solid removed by filtration
  5. concentrationthe organic phase was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c7f35cfaabf6438d87c639bb13301190
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150508B2

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