Reaktion #214908

Reaktionsgleichung

piperidine

6-(3,5-dioxomorpholino)hexyl p-toluenesulfonate

lithium hydride

→

4-(6-piperidinohexyl)-3,5-dioxomorpholine

Ausbeute 42.5%

Lösungsmittel

1,2-dimethoxyethane

1,2-dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Temperaturunder reflux for 22 hours
3. 3
   Filtrationthe resulting heterogeneous mixture filtered
4. 4
   Sonstigeto obtain a clear yellow filtrate
5. 5
   EinengenThe filtrate was concentrated to an orange oil which
6. 6
   workup.DISTILLATIONafter evaporative distillation (bath 120° C.; 0.05 torr.)

Vorschrift

To a mixture of 3.63 grams (9.84 millimoles) of 6-(3,5-dioxomorpholino)hexyl p-toluenesulfonate (prepared as described in Example IX) and 84.75 milligrams (10.7 millimoles) of lithium hydride in 10 milliliters of 1,2-dimethoxyethane was added 1.0 milliliter (10.0 millimoles) of piperidine in 10 milliliters of 1,2-dimethoxyethane. The mixture was heated under reflux for 22 hours, and the resulting heterogeneous mixture filtered to obtain a clear yellow filtrate. The filtrate was concentrated to an orange oil which after evaporative distillation (bath 120° C.; 0.05 torr.) produced 1.18 grams (42.5 percent yield) of 4-(6-piperidinohexyl)-3,5-dioxomorpholine base having infrared and nuclear magnetic resonance spectral characteristics appropriate for said compound. A 286.23 milligram (1.02 millimoles) sample of the free base, 4-(6-piperidinohexyl)-3,5-dioxomorpholine, was dissolved in 1.0 milliliter of 1 N sodium hydroxide (1.0 millimole) and the mixture concentrated to produce 289.63 grams (90 percent yield) of sodium [2-(6-piperidinohexyl)-amino-2-oxoethoxy]acetate product with the following spectral characteristics;

Quelle