Lithium amide → 1,1-Dimethyl-5-(3-phenylpropoxy)-2-pentynamine

HRID 981711

Reaktionsgleichung

Reaktionsgleichung von HRID 981711
[CH3:1][C:2]([NH2:6])([C:4]#[CH:5])[CH3:3].[Li+].[NH2-].Br[CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>N>[CH3:1][C:2]([CH3:3])([NH2:6])[C:4]#[C:5][CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 24532Lithium amideHCID 763193-Butyn-2-amine, 2-methyl-HCID 19797996(3-(2-Bromoethoxy)propyl)benzene

Produkt 1

HCID 137472431,1-Dimethyl-5-(3-phenylpropoxy)-2-pentynamineAusbeute 13,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 222AmmoniaLösungsmittel2×

Versuchsvorschrift

1,1-Dimethylpropargylamine (8.5 g) was added dropwise to a suspension of lithamide [from lithium (1.7 g)] in liquid ammonia (100 ml) at -33°. The mixture was stirred for 90 min and a solution of [3-(2-bromoethoxy)propyl]benzene (21.5 g) in ER (30 ml) was added dropwise. The suspension was stirred for 4 h and ammonia was allowed to evaporate overnight. The residue was treated with H2O (100 ml) and extracted with ER (3×100 ml). The dried extract was evaporated and the residue was distilled to give the title compound as a colourless oil (3.0 g) b.p. 160°-165°/0.2 mmHg. T.l.c. (ER) Rf 0.3.

Aufarbeitung

  1. stirringThe suspension was stirred for 4 h
  2. customto evaporate overnight
  3. additionThe residue was treated with H2O (100 ml)
  4. extractionextracted with ER (3×100 ml)
  5. extractionThe dried extract
  6. customwas evaporated
  7. distillationthe residue was distilled

Quellen und Nachweise

ORD-Eintrag
ord-80ae0c6680b34d6cb932a3c92c7f456a
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04992474

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