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

HRID 2051543Notes

Reaction equation

HRID 2051543 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.) soltuion 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 dissoled 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. washwashed with 10 percent hydrochloric acid (100 ml) and water (50 ml)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customleaving an oily solid which
  7. customwas crystallized from methanol-ethyl acetate-hexane

Sources & evidence

ORD record
ord-5003ff57a4614636a966e57c8557f851
Source dataset
uspto-grants-1991_05
Patent number
US05019597

Reaction notes

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