Diisopropylamine → HCID 19027240, Verbindung

HRID 2258276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2258276
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]=[N:21][C:22]([CH3:25])([CH3:24])[CH3:23].Br[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>O1CCCC1.C(Cl)Cl.O>[C:34]1([CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH:20]=[N:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Komponenten

8

Edukt 4

HCID 7912DiisopropylamineHCID 27356031-Bromo-7-phenylheptaneHCID 10866848HCID 10866848, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 19027240HCID 19027240, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a stirred solution of diisopropylamine (29.14 g,0.289 mol) in tetrahydrofuran (450 mL) cooled to -5° C. was added n-butyllithium (2.5M, 114.3 mL, 0.286 mol) at a rate which maintained the solution temperature below 10° C. After the addition was complete, the solution was stirred 15 min with cooling. To this solution was added N-[(2-methylphenyl)-methylene]-1,1-dimethylethanamine (50.0 g, 0.286 mol) in tetrahydrofuran (65.0 mL) at such a rate as to keep the reaction temperature below 5° C. The reaction was stirred for 15 min with cooling then 1-bromo-7-phenylheptane (72.9 g, 0.286 mol) in tetrahydrofuran (75 mL) was quickly added. The reaction mixture was stirred for 1 h with cooling then allowed to warm to room temperature and stirred for an additional 14 h. The reaction mixture was assayed by gas chromatography for product imine (RT 19.8 min., DB-1, 30 m×0.53 mm, program, 100° C. for 5 min, 100°-260° C. at 15° C./min, hold at 260° C. for 12 min.). The product was isolated by dilution of the reaction mixture with water and methylene chloride, quickly washing the organic mixture with water, and concentrating the solution to an oil. The oil was purified by distillation.

Aufarbeitung

  1. temperaturemaintained the solution temperature below 10° C
  2. additionAfter the addition
  3. temperaturewith cooling
  4. customthe reaction temperature below 5° C
  5. stirringThe reaction was stirred for 15 min
  6. temperaturewith cooling
  7. stirringThe reaction mixture was stirred for 1 h
  8. temperaturewith cooling
  9. stirringstirred for an additional 14 h
  10. washquickly washing the organic mixture with water
  11. concentrationconcentrating the solution to an oil
  12. distillationThe oil was purified by distillation

Quellen und Nachweise

ORD-Eintrag
ord-63fe0a47346142188c3c138fd5e39eff
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05659084

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