Amantadine → [(Adamantylcarbamoyl)methyl]phosphonic acid

HRID 1390247Notes

Reaction equation

HRID 1390247 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:12]([CH2:15][P:16](=[O:21])([O:19]C)[O:17]C)(O)=[O:13].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[C:1]12([NH:11][C:12]([CH2:15][P:16](=[O:17])([OH:21])[OH:19])=[O:13])[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 10868DicyclohexylcarbodiimideHCID 1899642-(Dimethoxyphosphoryl)acetic acid

Product 1

HCID 53941885[(Adamantylcarbamoyl)methyl]phosphonic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Adamantylamine (0.045 mole) and dimethyl (carboxymethyl)phosphonate (0.04 mole) were dissolved in 100 ml. of methylene chloride. As the solution was stirred, dicyclohexylcarbodiimide was added portionwise. The solution was stirred overnight, and the mixture filtered. The filtrate was concentrated to a solid. It was recrystallized from an appropriate solvent such as methanol. m.p. 190°-4° C.; yield, 32%

Workup

  1. stirringThe solution was stirred overnight
  2. filtrationthe mixture filtered
  3. concentrationThe filtrate was concentrated to a solid
  4. customIt was recrystallized from an appropriate solvent such as methanol
  5. customyield

Sources & evidence

ORD record
ord-32472d9a7b834fcd81f11d408b33063c
Source dataset
uspto-grants-1979_02
Patent number
US04138432

Reaction notes

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