Ethylenediamine → Amantadine

HRID 1488796Notes

Reaction equation

HRID 1488796 reaction equation
C1(C)C=CC(S(N)(=O)=O)=CC=1.[C:12]12([NH2:22])[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2.C(N)CC.C(N)CN.[Li]>CCOCC>[C:12]12([NH2:22])[CH2:19][CH:18]3[CH2:17][CH:16]([CH2:15][CH:14]([CH2:20]3)[CH2:13]1)[CH2:21]2

Participants

6

Reactant 4

HCID 3301EthylenediamineHCID 7852PropylamineHCID 3028194Lithium3×HCID 22906575HCID 22906575, compound2×

Product 1

HCID 2130Amantadine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Cleavage of 1-adamantanamine p-toluenesulfonamide. 1-Adamantanamine p-toluenesulfonamide (4 g, 0.13 mmol), n-propylamine (50 mL), and ethylenediamine (6.3 g, 0.11 mol) were placed in a 3 neck round bottomed flask equipped with a mechanical stirrer, condenser and thermometer. Lithium wire (0.64 g, 0.091 gram-atom) was added in two portions. Addition of one half of the lithium gave a dark color and the temperature rose to 42°. After an hour the temperature began to fall and the remainder of the lithium was added. The blue color dissipated over 45 min and the reaction mixture was poured onto ice and the resulting mixture was exacted with ether (3×50 mL). The ether was washed with brine and distilled at atmospheric pressure. The residue was sublimed at 90° (12 mm) to give 1.79 (91%) of 1-adamantanamine.

Workup

  1. customequipped with a mechanical stirrer, condenser
  2. customgave a dark color
  3. customrose to 42°
  4. waitAfter an hour the temperature began
  5. additionthe reaction mixture was poured onto ice
  6. washThe ether was washed with brine
  7. distillationdistilled at atmospheric pressure
  8. customwas sublimed at 90°

Sources & evidence

ORD record
ord-d99a59ac1dd34f6abeabbdebb8298a49
Source dataset
uspto-grants-1997_10
Patent number
US05675038

Reaction notes

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