Piperazine → HCID 20553731, compound

HRID 1106235Notes

Reaction equation

HRID 1106235 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:15])=[CH:10][CH:9]=2)[N:6]=1.[NH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.CS(O)(=O)=O>C(O)CCC>[C:16]1([S:14]([C:11]2[CH:12]=[CH:13][C:8]([CH2:7][C:5]3[N:6]=[C:2]([N:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)[S:3][CH:4]=3)=[CH:9][CH:10]=2)=[O:15])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 6395Methanesulfonic AcidHCID 20553732HCID 20553732, compound

Product 1

HCID 20553731HCID 20553731, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 6.4 g of 2-bromo-4-(4-phenylsulfinylbenzyl)thiazole (M. P. Kofler: 102° C.) and 6.5 g of anhydrous piperazine in 200 ml of butanol was refluxed for ten hours. Then, the solvent was evaporated and the thus obtained raw oil was taken off with 200 ml of a N solution of CH3SO3H. The insoluble matter was extracted twice with, each time, 20 ml of ether, then alkalized with K2CO3. The thus salted out oil was extracted twice with, each time, 50 ml of chloroform. The chloroform solution was washed with water, dried and evaporated. There was obtained 6.1 g of 1-[4-(4-phenylsulfinylbenzyl)-2-thiazolyl]piperazine, as semicrystallized product.

Workup

  1. customThen, the solvent was evaporated
  2. customthe thus obtained raw oil
  3. extractionThe insoluble matter was extracted twice with, each time, 20 ml of ether
  4. extractionwas extracted twice with, each time, 50 ml of chloroform
  5. washThe chloroform solution was washed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-4f09e925909b4546b3140f5d997f424b
Source dataset
uspto-grants-1982_01
Patent number
US04312869

Reaction notes

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