Sodium Hydroxide → Benzenamine, 2-chloro-N-(hexahydro-3H-thiazolo[3,4-a]pyridin-3-ylidene)-

HRID 654398Notes

Reaction equation

HRID 654398 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[CH2:17]O)=[S:10].[OH-].[Na+]>Br>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[C:9]1[N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]2[CH2:17][S:10]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 198871821-(2-Chlorophenylthiocarbamoyl)-2-hydroxymethylpiperidine

Product 1

HCID 14441922Benzenamine, 2-chloro-N-(hexahydro-3H-thiazolo[3,4-a]pyridin-3-ylidene)-

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

1 g 1-(2-Chlorophenylthiocarbamoyl)-2-hydroxymethylpiperidine in 20 ml 48% hydrobromic acid was heated under reflux for 2 hours. The mixture was then neutralised under cooling with 2N caustic soda, extracted with methylene chloride, the extracts dried over magnesium sulphate and the solvent distilled. The residue was recrystallised from diisopropyl ether.

Workup

  1. temperatureunder reflux for 2 hours
  2. extractionextracted with methylene chloride
  3. dry with materialthe extracts dried over magnesium sulphate
  4. distillationthe solvent distilled
  5. customThe residue was recrystallised from diisopropyl ether

Sources & evidence

ORD record
ord-4567102542284015835a0d99ac91f6c5
Source dataset
uspto-grants-1992_07
Patent number
US05131946

Reaction notes

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