3-[2-(1-Piperazinyl)ethyl]-2-oxazolidinone → HCID 21481136, compound

HRID 435711Notes

Reaction equation

HRID 435711 reaction equation
Cl[CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][C:5]2[CH:13]=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[CH:16][C:4]=2[CH2:3]1.[N:21]1([CH2:27][CH2:28][N:29]2[CH2:33][CH2:32][O:31][C:30]2=[O:34])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>C(Cl)(Cl)Cl>[F:18][C:17]([F:20])([F:19])[C:15]1[CH:14]=[CH:13][C:5]2[S:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[CH:2]([N:24]3[CH2:25][CH2:26][N:21]([CH2:27][CH2:28][N:29]4[CH2:33][CH2:32][O:31][C:30]4=[O:34])[CH2:22][CH2:23]3)[CH2:3][C:4]=2[CH:16]=1

Participants

4

Reactant 2

HCID 122755453-[2-(1-Piperazinyl)ethyl]-2-oxazolidinoneHCID 15619006HCID 15619006, compound

Product 1

HCID 21481136HCID 21481136, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

17 g of 10-chloro-10,11-dihydro-2-trifluoromethyl-dibenzo[b,f]thiepin in 90 ml of chloroform and 26.2 g of 3-[2-(1-piperazinyl)-ethyl]-2-oxazolidinone are heated under reflux for 14 hours. The mixture is evaporated and the residue treated with ice-water, ether and 2-N aqueous sodium hydroxide. After equilibration, the organic phase is washed with water and acidified with ethanolic hydrochloric acid. The precipitate which separates is filtered off and dissolved in about 400 ml of water. The aqueous solution is extracted with ether. The aqueous solution is treated with ice, made alkaline with aqueous sodium hydroxide solution and extracted with about 350 ml of benzene. The benzene phase is dried over sodium sulphate, filtered and evaporated. There is obtained 3-[2-[4-(10,11-dihydro-2-trifluoromethyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl]-2 -oxazolidinone as an oil. By treatment with maleic acid there is obtained the corresponding maleate which is crystallised from ethanol/ether; melting point 168°-169° C.

Workup

  1. temperatureunder reflux for 14 hours
  2. customThe mixture is evaporated
  3. additionthe residue treated with ice-water, ether and 2-N aqueous sodium hydroxide
  4. washAfter equilibration, the organic phase is washed with water
  5. filtrationThe precipitate which separates is filtered off
  6. dissolutiondissolved in about 400 ml of water
  7. extractionThe aqueous solution is extracted with ether
  8. additionThe aqueous solution is treated with ice
  9. extractionextracted with about 350 ml of benzene
  10. dry with materialThe benzene phase is dried over sodium sulphate
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-ae0fd6ea51454fda822ba22c7181a107
Source dataset
uspto-grants-1977_02
Patent number
US04006144

Reaction notes

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