Amantadine → HCID 4540425, compound

HRID 1081476Notes

Reaction equation

HRID 1081476 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]12[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[C:22]([N+]([O-])=O)[CH:21]=1>CCO>[C:9]12([NH:8][C:24]3[CH:25]=[C:20]([Cl:19])[CH:21]=[CH:22][C:23]=3[N+:26]([O-:28])=[O:27])[CH2:10][CH:11]3[CH2:17][CH:15]([CH2:14][CH:13]([CH2:12]3)[CH2:18]1)[CH2:16]2

Participants

5

Reactant 3

HCID 2130AmantadineHCID 8471TriethylamineHCID 330974-Chloro-1,2-dinitrobenzene

Product 1

HCID 4540425HCID 4540425, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

15.5 ml of triethylamine and then a suspension of 15 g of 1-aminoadamantane in 50 ml of 96° EtOH are added to a solution of 20 g of 4-chloro-1,2-dinitrobenzene in 80 ml of 96° EtOH. The mixture is refluxed for 7 hours and, after cooling, the precipitate formed is filtered off to give 7 g of the expected product. M.p.=146° C.

Workup

  1. temperatureThe mixture is refluxed for 7 hours
  2. temperatureafter cooling
  3. customthe precipitate formed
  4. filtrationis filtered off

Sources & evidence

ORD record
ord-1a5620f6e61f46d0bf1b549557af3abd
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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