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

HRID 66089

Reaction equation

HRID 66089 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-17014710960f4dae85ffe803714eb7bb
Source dataset
uspto-grants-1978_12
Patent number
US04130561

Linked notes

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