Amantadine → HCID 53941885, compound

HRID 371701

Reaction equation

HRID 371701 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 53941885HCID 53941885, compound

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-9a8e205786444e46bdd7c9cade08ae9e
Source dataset
uspto-grants-1978_05
Patent number
US04087522

Linked notes

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