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

HRID 1707115Notes

Reaction equation

HRID 1707115 reaction equation
[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

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 3028194LithiumHCID 130653214-(4-Chloro-2-fluorophenyl)-4-cyano-1-methylpiperidineHCID 23689305HCID 23689305, compound

Product 1

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

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

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 water, 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].

Workup

  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 water
  9. customdried
  10. customevaporated to dryness
  11. customleaving a white crystalline solid
  12. customThe solid is recrystallized from an acetone-pentane mixture

Sources & evidence

ORD record
ord-2753b6537641487188151566fd95b7a6
Source dataset
uspto-grants-1980_06
Patent number
US04209625

Reaction notes

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