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

HRID 1748696

Reaction equation

HRID 1748696 reaction equation
[C:1]12([NH2:11])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(N(CC)CC)C.[C:19](Cl)(=[O:22])[CH:20]=[CH2:21]>C1COCC1>[C:1]12([NH:11][C:19](=[O:22])[CH:20]=[CH2:21])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

5

Reactant 3

HCID 2130AmantadineHCID 8471TriethylamineHCID 13140Acryloyl chloride

Product 1

HCID 284637N-(Adamantan-1-yl)prop-2-enimidic acidYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Adamantylamine (0.76 g; 5.0 mmol) and triethylamine (0.77 ml; 5.5 mmol) were dissolved in dry THF (40 mL) on an ice bath. After dropping acryloyl chloride (0.45 ml; 5.5 mmol) onto the solution, the mixture was stirred for 4 hours. After the reaction, the precipitate was removed by filtration, and the supernatant liquid was concentrated under reduced pressure. The resulting crude product was recrystallized from chloroform to give N-(1-adamantyl)acrylamide (0.85 mg; yield: 83%).

Workup

  1. customAfter the reaction
  2. customthe precipitate was removed by filtration
  3. concentrationthe supernatant liquid was concentrated under reduced pressure
  4. customThe resulting crude product was recrystallized from chloroform

Sources & evidence

ORD record
ord-f68d3521c38c43e1b183e0ec68c0dd61
Source dataset
uspto-grants-2015_10
Patent number
US09150762B2

Linked notes

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