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

HRID 66089

反応式

HRID 66089 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-17014710960f4dae85ffe803714eb7bb
出典データセット
uspto-grants-1978_12
特許番号
US04130561

関連ノート

読み込み中…