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

HRID 1487025

Reaktionsgleichung

Reaktionsgleichung von HRID 1487025
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 (1 M LHMDS in THF, 15 mL, 15.00 mmol) under nitrogen. The reaction mixture was heated to 70° C. for 45 minutes 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) as an orange oil. LCMS [LCMS1] Rt 1.03 min, m/z (ES+) 178 (M+H).

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-c561e36556e34bc0ab77e7f6e38f36d6
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428452B2

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