Amantadine → HCID 19428543, compound

HRID 1721291Notes

Reaction equation

HRID 1721291 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 containing 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 is boiled under reflux for 75 hours, then evaporated. The evaporation residue is suspended in 400 ml of ether, the suspension is filtered off and, after drying, the product filtered off is purified by chromatography on a silica gel column. By using chloroform as eluent and recrystallizing the obtained product 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 75 hours
  2. customevaporated
  3. filtrationthe suspension is filtered off
  4. customafter drying
  5. filtrationthe product filtered off
  6. customis purified by chromatography on a silica gel column
  7. customrecrystallizing the obtained product from ether the title compound
  8. customis obtained in a yield of 23.94 g (66.44%), m.p.: 232°-236° C.

Sources & evidence

ORD record
ord-c92cf6e2c91249d5878a97ebd5b2a38d
Source dataset
uspto-grants-1996_04
Patent number
US05510345

Reaction notes

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