Tert-Butylamine → HCID 89422940, Verbindung

HRID 1481680Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1481680
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12](=O)[CH2:13][CH2:14][CH3:15])=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.[CH3:17][C:18]([NH2:21])([CH3:20])[CH3:19]>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH3:17][C:18]([N:21]=[C:12]([C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[N:2]([CH3:1])[CH2:3][CH2:4][CH2:5]2)[CH2:13][CH2:14][CH3:15])([CH3:20])[CH3:19]

Komponenten

5

Edukt 2

HCID 6385Tert-ButylamineHCID 39104401HCID 39104401, Verbindung

Produkt 1

HCID 89422940HCID 89422940, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)butan-1-one (2.94 g, 13.5 mmol) in CH2Cl2 (14 mL) was added 2-methylpropan-2-amine (5.7 mL, 54.2 mmol, 4.0 eq). The mixture was cooled to 0° C. before TiCl4 (1.0M in CH2Cl2, 8.8 mL, 8.8 mmol, 0.65 eq) was added via syringe pump over 30 min. The reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was quenched with saturated aqueous NaHCO3 (15 mL) then extracted by CH2Cl2 (5×25 mL). The combined organic layers were dried over Na2SO4 then concentrated to give a crude product which was carried over to next step without further purification. LC-MS 273.1 [M+H]+, RT 0.65 min. (1 min Method).

Aufarbeitung

  1. additionwas added via syringe pump over 30 min
  2. customThe reaction mixture was quenched with saturated aqueous NaHCO3 (15 mL)
  3. extractionthen extracted by CH2Cl2 (5×25 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationthen concentrated

Quellen und Nachweise

ORD-Eintrag
ord-9b2bb029956d44299353139e2611a6a5
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409905B2

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