Sodium Hydroxide → HCID 86734368, compound

HRID 1414529Notes

Reaction equation

HRID 1414529 reaction equation
Cl.N1C=CC=CC=1.C([O:10][C:11]1[C:16]2[S:17][C:18]3[C:23]([C:24]4([CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)[C:15]=2[CH:14]=[CH:13][CH:12]=1)=[CH:22][CH:21]=[CH:20][CH:19]=3)C.[OH-].[Na+]>O>[OH:10][C:11]1[C:16]2[S:17][C:18]3[C:23]([C:24]4([CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)[C:15]=2[CH:14]=[CH:13][CH:12]=1)=[CH:22][CH:21]=[CH:20][CH:19]=3

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 10176127Pyridinium chlorideHCID 86734369HCID 86734369, compound

Product 1

HCID 86734368HCID 86734368, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
210 °C

Procedure

To a melt of pyridine hydrochloride (19 g.) at 160° C. is added 4-ethoxy-1'-methylthioxanthene-9-spiro-4'-piperidine (1.3 g.). The stirred mixture is heated to 210° C. for 30 minutes and then cooled, diluted with water and made alkaline with aqueous sodium hydroxide solution. A small amount of solid material is removed by filtration and the filtrate is acidified with concentrated hydrochloric acid followed by neutralisation with sodium bicarbonate and extraction with chloroform. The chloroform extract is evaporated to dryness and the residual yellow gum crystallised from aqueous ethanol to give 4-hydroxy-1'-methylthioxanthene-9-spiro-4'-piperidine, m.p. 180°-182° C.

Workup

  1. temperaturecooled
  2. customA small amount of solid material is removed by filtration
  3. extractionfollowed by neutralisation with sodium bicarbonate and extraction with chloroform
  4. extractionThe chloroform extract
  5. customis evaporated to dryness
  6. customthe residual yellow gum crystallised from aqueous ethanol

Sources & evidence

ORD record
ord-7888bcacbac94831a654bcf8b3330b38
Source dataset
uspto-grants-1977_01
Patent number
US04001418

Reaction notes

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