Amantadine → HCID 19428543, compound

HRID 1078285Notes

Reaction equation

HRID 1078285 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][C:10]23[CH2:19][CH:14]4[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]4)[CH2:11]2)[CH2:17]3)[N:3]=1.[NH2:20][C:21]12[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]3)[CH2:22]1)[CH2:28]2>C(O)CCC>[C:10]12([NH:9][C:4]3[N:3]=[C:2]([NH:20][C:21]45[CH2:22][CH:23]6[CH2:29][CH:27]([CH2:26][CH:25]([CH2:24]6)[CH2:30]4)[CH2:28]5)[CH:7]=[C:6]([Cl:8])[N:5]=3)[CH2:17][CH:16]3[CH2:18][CH:12]([CH2:13][CH:14]([CH2:15]3)[CH2:19]1)[CH2:11]2

Participants

4

Reactant 2

HCID 2130AmantadineHCID 19428536HCID 19428536, compound

Product 1

HCID 19428543HCID 19428543, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 26.0 g (87.25 mmoles) of 4,6-dichloro-2-(1-adamantylamino)pyrimidine and 39.5 g (261.6 mmoles) of 1-aminoadamantane in 200 ml of n-butanol, the reaction mixture is boiled under reflux for 24 hours, and evaporated. The residue is suspended in 400 ml of ether and filtered off. After drying, the filtered-off residue is purified by chromatography on a silica gel column and eluted with chloroform. After recrystallization from ether, the title compound is obtained in a yield of 23.94 g (66.44%), m.p.: 232°-236° C.

Workup

  1. temperatureunder reflux for 24 hours
  2. customevaporated
  3. filtrationfiltered off
  4. customAfter drying
  5. customthe filtered-off residue is purified by chromatography on a silica gel column
  6. washeluted with chloroform
  7. customAfter recrystallization from ether

Sources & evidence

ORD record
ord-0c93825290854db9af4d40871317748d
Source dataset
uspto-grants-1996_08
Patent number
US05547949

Reaction notes

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