Amantadine → N-(Adamantan-1-yl)prop-2-enimidic acid

HRID 1748696

Reaktionsgleichung

Reaktionsgleichung von HRID 1748696
[C:1]12([NH2:11])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(N(CC)CC)C.[C:19](Cl)(=[O:22])[CH:20]=[CH2:21]>C1COCC1>[C:1]12([NH:11][C:19](=[O:22])[CH:20]=[CH2:21])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Komponenten

5

Edukt 3

HCID 2130AmantadineHCID 8471TriethylamineHCID 13140Acryloyl chloride

Produkt 1

HCID 284637N-(Adamantan-1-yl)prop-2-enimidic acidAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1-Adamantylamine (0.76 g; 5.0 mmol) and triethylamine (0.77 ml; 5.5 mmol) were dissolved in dry THF (40 mL) on an ice bath. After dropping acryloyl chloride (0.45 ml; 5.5 mmol) onto the solution, the mixture was stirred for 4 hours. After the reaction, the precipitate was removed by filtration, and the supernatant liquid was concentrated under reduced pressure. The resulting crude product was recrystallized from chloroform to give N-(1-adamantyl)acrylamide (0.85 mg; yield: 83%).

Aufarbeitung

  1. customAfter the reaction
  2. customthe precipitate was removed by filtration
  3. concentrationthe supernatant liquid was concentrated under reduced pressure
  4. customThe resulting crude product was recrystallized from chloroform

Quellen und Nachweise

ORD-Eintrag
ord-f68d3521c38c43e1b183e0ec68c0dd61
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150762B2

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