Amantadine → N-(4-nitrophenyl)adamantan-1-amine

HRID 2050206Notes

Reaction equation

HRID 2050206 reaction equation
[CH2:1]1[CH:6]2[CH2:7][C:8]3([NH2:11])[CH2:10][CH:4]([CH2:5]2)[CH2:3][CH:2]1[CH2:9]3.F[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].CN(P(N(C)C)(N(C)C)=O)C>O>[C:8]12([NH:11][C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=3)[CH2:10][CH:4]3[CH2:5][CH:6]([CH2:1][CH:2]([CH2:3]3)[CH2:9]1)[CH2:7]2

Participants

6

Reactant 4

HCID 2130AmantadineHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 12679Hexamethylphosphoramide

Product 1

HCID 12510269N-(4-nitrophenyl)adamantan-1-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.51 g. (0.01 mole) of 1-adamantamine, 1.41 g. p-fluoronitrobenzene and 1.38 g. K2CO3 in 10 ml. HMPA was stirred overnight in an oil bath at 135°. The mixture was allowed to cool, diluted with H2O and extracted thoroughly with C6H6. The organic layer was washed in turn with H2O and brine and taken to dryness. The waxy residue was recrystallized twice from Me2CO:cyclohexane to give 1.82 g. (67%) of N,1-adamantyl-p-nitroaniline, m.p. 188°-189°.

Workup

  1. additionA mixture of 1.51 g
  2. temperatureto cool
  3. extractionextracted thoroughly with C6H6
  4. washThe organic layer was washed in turn with H2O and brine
  5. customThe waxy residue was recrystallized twice from Me2CO
  6. customcyclohexane to give 1.82 g

Sources & evidence

ORD record
ord-ceb5eb79161c4b0481d072be70933f54
Source dataset
uspto-grants-1980_04
Patent number
US04200588

Reaction notes

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