Sodium Hydroxide → 6-Chloro-1'-methylspiro[indoline-3,4'-piperidine]

HRID 67216ノート

反応式

HRID 67216 の反応式
[H-].C(O[Al](OCC)OCC)C.[Li+].[Li].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2([C:28]#[N:29])[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]2)=[C:17](F)[CH:16]=1.[OH-].[Na+]>C(COC)OC.O.C(O)C>[Cl:14][C:15]1[CH:20]=[C:19]2[NH:29][CH2:28][C:21]3([CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)[C:18]2=[CH:17][CH:16]=1

参加物

8

反応物 4

HCID 14798Sodium HydroxideHCID 3028194LithiumHCID 130653214-(4-Chloro-2-fluorophenyl)-4-cyano-1-methylpiperidineHCID 23689305HCID 23689305、化合物

生成物 1

HCID 128016176-Chloro-1'-methylspiro[indoline-3,4'-piperidine]

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒2 回

実験手順

To a refluxing suspension of lithium triethoxyaluminum hydride (prepared by dropping 12 ml of absolute ethyl alcohol carefully into a cooled slurry of 4.9 g of lithium aluminumhydride in 150 ml of glyme) is added over a 30 minute span a mixture of 8.1 g of 4-(4'-chloro-2-fluorophenyl)-4-cyano-1-methylpiperidine in 80 ml of glyme. After total addition, stirring is continued at reflux for 72 hours. Thereafter, the mixture is permitted to cool before successively adding 5 ml of water, 5 ml of a 15% aqueous sodium hydroxide solution and 15 ml of water effecting a precipitate. The precipitate is collected by filtration followed by repeated washings with warm methylene chloride. The filtrate, combined with the washings, is successively washed with waer, dried and evaporated to dryness leaving a white crystalline solid. The solid is recrystallized from an acetone-pentane mixture to provide fine needles, mp 172°-173° C. of 6-chloro-1'-methylspiro[indoline-3,4'-piperidine].

後処理

  1. customprepared
  2. additionis added over a 30 minute span
  3. additionAfter total addition
  4. temperatureat reflux for 72 hours
  5. temperatureto cool
  6. filtrationThe precipitate is collected by filtration
  7. washwashings with warm methylene chloride
  8. washis successively washed with waer
  9. customdried
  10. customevaporated to dryness
  11. customleaving a white crystalline solid
  12. customThe solid is recrystallized from an acetone-pentane mixture

出典と根拠

ORDレコード
ord-0fec9dd568d249649770a84363631cc0
出典データセット
uspto-grants-1982_08
特許番号
US04345081

反応ノート

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