Amantadine → HCID 20551999, compound

HRID 1446970Notes

Reaction equation

HRID 1446970 reaction equation
[NH2:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.C(N(CC)CC)C.Cl[C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21]>ClCCl>[CH2:23]([O:22][C:20]([NH:1][C:2]12[CH2:3][CH:4]3[CH2:10][CH:8]([CH2:7][CH:6]([CH2:5]3)[CH2:11]1)[CH2:9]2)=[O:21])[CH:24]=[CH2:25]

Participants

5

Reactant 3

HCID 2130AmantadineHCID 8471TriethylamineHCID 18052Allyl chloroformate

Product 1

HCID 20551999HCID 20551999, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Aminoadamantane (10 mmol; 1.51 g) and triethylamine (1.9 ml) in dry dichloromethane (30 ml) are stirred at 0°-5° C. and allyl chloroformate (1.1 ml) added dropwise. After 0.5 hour, the solution is washed with dilute sulfuric acid and water. After drying over anhydrous magnesium sulfate, the solution is evaporated to give 1-(allyloxycarbonylamino)adamantane, as a white solid, with a melting point of about 56°-58° C.

Workup

  1. washthe solution is washed with dilute sulfuric acid and water
  2. dry with materialAfter drying over anhydrous magnesium sulfate
  3. customthe solution is evaporated

Sources & evidence

ORD record
ord-7e2e2a72dceb42e4b13022edf3ba538b
Source dataset
uspto-grants-1982_02
Patent number
US04314942

Reaction notes

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