Reaktion #312377

Reaktionsgleichung

N-methyl-morpholine

water

6-methyl-8β-hydrazino-methyl-ergoline

N-methyl-morpholine

acetyl chloride

ammonia

→

6-methyl-8β-([N'-acetyl-hydrazino]-methyl)-ergoline

Ausbeute 72.4%

Lösungsmittel

chloroform

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONWhen the solid dissolves completely
2. 2
   workup.ADDITIONAfter the addition the pH of the mixture
3. 3
   workup.ADDITIONis introduced
4. 4
   workup.STIRRINGThe mixture is shaken
5. 5
   Sonstigethe phases are separated from each other, the organic phase
6. 6
   Waschenis washed twice with water
7. 7
   Sonstigedried
8. 8
   Sonstigeevaporated to dryness in vacuo
9. 9
   SonstigeThe dry residue is crystallized from ethanol
10. 10
    FiltrationThe separated crystals are filtered off
11. 11
    Waschenwashed with a small amount of cold (5° C.) ethanol
12. 12
    Sonstigedried in vacuo

Vorschrift

0.6 g (0.0021 moles) of 6-methyl-8β-hydrazino-methyl-ergoline are introduced, under vigorous stirring, into a solution of 0.28 ml (0.0025 moles) of N-methyl-morpholine in 60 ml of dry chloroform. When the solid dissolves completely, a solution of 0.184 g (0.0023 moles) of acetyl chloride in 2 ml of acetonitrile is added dropwise, within 5 minutes, to the mixture. After the addition the pH of the mixture is checked, and when it is lower than 6, N-methyl-morpholine is introduced. The reaction mixture is stirred at room temperature for one hour, thereafter it is diluted with 30 ml of water, and the pH of the mixture is adjusted to 8 with aqueous ammonia. The mixture is shaken, the phases are separated from each other, the organic phase is washed twice with water, dried, and evaporated to dryness in vacuo. The dry residue is crystallized from ethanol. The separated crystals are filtered off, washed with a small amount of cold (5° C.) ethanol, and dried in vacuo. 0.5 g (72.4%) of 6-methyl-8β-([N'-acetyl-hydrazino]-methyl)-ergoline are obtained; m.p.: 213°-215° C., [α]D20 =-38.7° (c=1, in 96% ethanol).

Quelle