Hydrogen Bromide → HCID 18941037, compound

HRID 356120Notes

Reaction equation

HRID 356120 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][C:13]2[S:14][C:15]3[CH2:24][C:23]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[C:16]=3[N:17]=2)[CH2:8][CH2:7]1)=O)C.Br.[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.O>[NH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][C:13]2[S:14][C:15]3[CH2:24][C:23]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[C:16]=3[N:17]=2)[CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 18940963HCID 18940963, compound

Product 1

HCID 18941037HCID 18941037, compoundYield 116.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To 0.25 g of 2-[(1-ethoxycarbonyl-4-piperidyl)methyl]-8H-indeno[1,2-d]thiazole was added 10 ml of a 25% solution of hydrogen bromide in acetic acid, followed by heating under reflux for one hour. After cooling, water was added, and the mixture was alkalized with a 1N aqueous solution of sodium hydroxide and potassium carbonate, followed by extraction with chloroform. The extract was dried over anhydrous potassium carbonate. The solvent was then evaporated, whereby 0.23 g of 2-(4-piperidylmethyl)-8H-indeno[1,2-d]thiazole was obtained. The resulting product was dissolved in methanol, fumaric acid was added thereto, followed by crystallization from acetonitrile. The crystals were recrystallized from acetonitrile-methanol to give a fumarate.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for one hour
  3. temperatureAfter cooling
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe extract was dried over anhydrous potassium carbonate
  6. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-5981fb7f80b74b8ca917b11d1f59b228
Source dataset
uspto-grants-1998_11
Patent number
US05834499

Reaction notes

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