Amantadine → HCID 58794622, compound

HRID 239792

Reaction equation

HRID 239792 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

HCID 58794622HCID 58794622, compound

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-760c5daef6d943b2abc73398a3bb4059
Source dataset
uspto-grants-2014_02
Patent number
US08642801B2

Linked notes

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