Amantadine → HCID 178480597, compound

HRID 2052069Notes

Reaction equation

HRID 2052069 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.[CH2:12]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])C.[NH2:19][C:20]1[N:21]([CH3:25])[CH:22]=[CH:23][N:24]=1.[OH-].[Na+]>C(Cl)Cl>[C:1]12([NH:11][C:12]([N:14]3[CH2:17][CH2:18][CH2:16][CH2:15]3)=[N:19][C:20]3[N:21]([CH3:25])[CH:22]=[CH:23][N:24]=3)[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

6

Reactant 4

HCID 2130AmantadineHCID 8471Triethylamine2×HCID 14798Sodium HydroxideHCID 5663211-Methyl-1H-imidazol-2-amine

Product 1

HCID 178480597HCID 178480597, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To 18.85 g (0.1 mole) of dichloromethylenetetramethylene ammonium chloride in 100 ml of dry methylene chloride is added dropwise a solution of 15.13 g (0.1 mole) of 1-adamantylamine and 20.2 g (0.2 mole) of triethylamine in dry CH2Cl2 with cooling (ice bath) under dry N2. After the addition is complete, the mixture is stirred at room temperature for 3 hrs. Then a dry methylene chloride solution containing 9.71 g (0.1 mole) of 2-amino-1-methylimidazole and 10.1 g (0.1 mole) of triethylamine is added dropwise over 1 hr with cooling. After the addition the mixture is stirred under dry N2 overnight at room temperature. The mixture is then shaken with excess 3 N NaOH and the organic layer is separated, dried (K2CO3), filtered and the solvent and residual triethylamine is removed in vacuo giving N-(1-adamantyl)-N'-(1-methylimidazol-2-yl)-1-pyrrolidinecarboximidamide free base.

Workup

  1. temperaturewith cooling (ice bath) under dry N2
  2. additionAfter the addition
  3. additionis added dropwise over 1 hr
  4. temperaturewith cooling
  5. additionAfter the addition the mixture
  6. stirringis stirred under dry N2 overnight at room temperature
  7. customthe organic layer is separated
  8. dry with materialdried (K2CO3)
  9. filtrationfiltered
  10. customthe solvent and residual triethylamine is removed in vacuo

Sources & evidence

ORD record
ord-7b51b4170e2644a89f39fe9487543225
Source dataset
uspto-grants-1980_01
Patent number
US04182865

Reaction notes

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