Amantadine → HCID 19428543, compound

HRID 1078305Notes

Reaction equation

HRID 1078305 reaction equation
[C:1]12([NH:11][C:12]3[CH:17]=[C:16]([Cl:18])[N:15]=[C:14](Cl)[N:13]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[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:21]12([NH:20][C:14]3[N:13]=[C:12]([NH:11][C:1]45[CH2:2][CH:3]6[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]6)[CH2:8]4)[CH2:10]5)[CH:17]=[C:16]([Cl:18])[N:15]=3)[CH2:22][CH:23]3[CH2:29][CH:27]([CH2:26][CH:25]([CH2:24]3)[CH2:30]1)[CH2:28]2

Participants

4

Reactant 2

HCID 2130AmantadineHCID 19428531HCID 19428531, compound

Product 1

HCID 19428543HCID 19428543, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

26.0 g (87.25 mmoles) of 4-(1-adamantylamino)-2,6-dichloropyrimidine and 39.5 g (261.6 mmoles) of 1-aminoadamantane are dissolved in 200 ml of n-butanol, the reaction mixture is boiled for 75 hours and evaporated. The residue is suspended in 400 ml of ether and filtered. The filtered substance is chromatographed after drying on a silica gel column by using chloroform as eluent. The substance obtained is a mixture of the title isomers. The isomers are separated on a silica gel column by using as eluent a 49:1 mixture of hexane and ethyl acetate. 2,4-Bis(1-adamantylamino)-6-chloropyrimidine is obtained which is recrystallized from hexane to obtain a yield of 21.67 g (60.14%). Its melting point and 1H-NMR are identical to those of the product according to Example 11.

Workup

  1. customevaporated
  2. filtrationfiltered
  3. customThe filtered substance is chromatographed
  4. customafter drying on a silica gel column
  5. customThe substance obtained
  6. additiona mixture of the title isomers
  7. customThe isomers are separated on a silica gel column
  8. additiona 49:1 mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-8718fea7988343809ff1ae6fda5b4ece
Source dataset
uspto-grants-1996_08
Patent number
US05547949

Reaction notes

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