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

HRID 66089

반응식

HRID 66089 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-17014710960f4dae85ffe803714eb7bb
출처 데이터셋
uspto-grants-1978_12
특허 번호
US04130561

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