Amantadine → HCID 58794622, Verbindung

HRID 239792

Reaktionsgleichung

Reaktionsgleichung von HRID 239792
[C:1]12(N)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:12][CH:13]1[S:17](=[O:19])(=[O:18])[O:16][CH2:15][CH2:14]1.C(#[N:22])C>>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:22][CH2:15][CH2:14][CH:13]([S:17]([OH:16])(=[O:19])=[O:18])[CH3:12])[CH2:8]2

Komponenten

4

Edukt 3

HCID 2130AmantadineHCID 6342AcetonitrileHCID 707161,2-Oxathiolane, 3-methyl-, 2,2-dioxide

Produkt 1

HCID 58794622HCID 58794622, Verbindung

Versuchsvorschrift

To a solution of 1-adamantanamine (1.99 g, 13.1 mmol) in acetonitrile (15 mL) was added 2,4-butane sultone (1.87 g, 13.8 mmol). The solution was stirred at reflux for 2 hours. The reaction was cooled to room temperature. The solid was collected by filtration, washed with acetonitrile (2×25 mL) and dried in vacuo. 1H NMR (DMSO, 500 MHz) δ ppm 3.20 (m, 1H), 3.05 (m, 2H), 2.67 (m, 1H), 2.07 (m, 2H), 2.00 (m, 1H), 1.95 (m, 4H), 1.82 (m, 4H), 1.69 (m, 4H), 1.55 (m, 4H), 1.12 (d, 1H, J=8.0 Hz). 13C (DMSO, 125 MHz) δ ppm 62.27, 53.91, 44.33, 37.30, 36.82, 36.77, 30.30, 30.20, 29.57, 29.50, 28.95, 17.12, 26.85, 17.44. ES-MS 288 (M+1).

Aufarbeitung

  1. temperatureat reflux for 2 hours
  2. filtrationThe solid was collected by filtration
  3. washwashed with acetonitrile (2×25 mL)
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-760c5daef6d943b2abc73398a3bb4059
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642801B2

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