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

HRID 5494

Reaction equation

HRID 5494 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[C:6]12([NH2:16])[CH2:15][CH:10]3[CH2:11][CH:12]([CH2:14][CH:8]([CH2:9]3)[CH2:7]1)[CH2:13]2.C(N(CC)CC)C>C(OCC)C>[C:6]12([NH:16][C:1](=[O:4])[CH:2]=[CH2:3])[CH2:13][CH:12]3[CH2:11][CH:10]([CH2:9][CH:8]([CH2:14]3)[CH2:7]1)[CH2:15]2

Participants

5

Reactant 3

HCID 2130AmantadineHCID 8471TriethylamineHCID 13140Acryloyl chloride

Product 1

HCID 284637N-(Adamantan-1-yl)prop-2-enimidic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of acryloyl chloride (4.05 ml, 0.05 mole) in ethyl ether (25 ml) was added to a cold (+5° C.) solution of 1-adamantaneamine (7.65 g, 0.05 mole) and triethylamine (15.3 ml, 0.11 mole) in ethyl ether (300 ml) and the solution stirred for 72 hours at room temperature. The solvent was removed on a rotary evaporator. The residue was dissolved in ethyl acetate (100 ml), washed with 10 percent hydrochloric acid (100 ml) and water (50 ml), dried over sodium sulfate, filtered and the solvent removed in vacuo leaving an oily solid which was crystallized from methanol-ethyl acetate-hexane. The structure was confirmed by NMR.

Workup

  1. customThe solvent was removed on a rotary evaporator
  2. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
  3. washwashed with 10 percent hydrochloric acid (100 ml) and water (50 ml)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customleaving an oily solid which
  8. customwas crystallized from methanol-ethyl acetate-hexane

Sources & evidence

ORD record
ord-d5fd9102081148d99300a6c311bae329
Source dataset
uspto-grants-1993_09
Patent number
US05244899

Linked notes

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