Amantadine → 3-Adamant-1-ylcarbamoyl-1,2,4-oxadiazole

HRID 1730036Notes

Reaction equation

HRID 1730036 reaction equation
[N:1]([C:4]([C:6]1[N:10]=[CH:9][O:8][N:7]=1)=[O:5])=[N+]=[N-].N[C:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2>C(Cl)(Cl)Cl>[C:12]12([NH:1][C:4]([C:6]3[N:10]=[CH:9][O:8][N:7]=3)=[O:5])[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2

Participants

4

Reactant 2

HCID 2130AmantadineHCID 214988371,2,4-Oxadiazole-3-carbonyl azide

Product 1

HCID 214988293-Adamant-1-ylcarbamoyl-1,2,4-oxadiazoleYield 27%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Azidocarbonyl-1,2,4-oxadiazole (350 mg.) was added to a solution of 1-aminoadamantane (378 mg.) in chloroform (15 ml.) and the mixture was stirred for 24 hr. The chloroform solution was evaporated to dryness under reduced pressure and the residue was recrystallised from aqueous methanol to give title compound (167 mg.), m.p. 141°-142°, νmax. (EtOH) 230 nm (ε 3,910), λmax. (Nujol) 3392 (--NH--) 1692 and 1515 cm.-1 (CONH). Further examples provided in Table II were prepared by the following general methods:

Workup

  1. customThe chloroform solution was evaporated to dryness under reduced pressure
  2. customthe residue was recrystallised from aqueous methanol

Sources & evidence

ORD record
ord-c0f9b0063d134453b8a37759ce16b04c
Source dataset
uspto-grants-1976_11
Patent number
US03991067

Reaction notes

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