3-[2-(1-Piperazinyl)ethyl]-2-oxazolidinone → HCID 21481144, compound

HRID 435708Notes

Reaction equation

HRID 435708 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]([S:17](=[O:22])(=[O:21])[N:18]([CH3:20])[CH3:19])=[CH:16][C:4]=2[CH2:3]1.[N:23]1([CH2:29][CH2:30][N:31]2[CH2:35][CH2:34][O:33][C:32]2=[O:36])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>C(Cl)(Cl)Cl>[CH3:19][N:18]([CH3:20])[S:17]([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:26]3[CH2:27][CH2:28][N:23]([CH2:29][CH2:30][N:31]4[CH2:35][CH2:34][O:33][C:32]4=[O:36])[CH2:24][CH2:25]3)[CH2:3][C:4]=2[CH:16]=1)(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 122755453-[2-(1-Piperazinyl)ethyl]-2-oxazolidinoneHCID 1561900510-Chloro-10,11-dihydro-2-dimethylsulphamoyl-dibenzo[b,f]thiepin

Product 1

HCID 21481144HCID 21481144, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

11.9 g of 10-chloro-10,11-dihydro-2-dimethylsulphamoyldibenzo[b,f]thiepin in 250 ml of chloroform are treated with 20 g of 3-[2-(1-piperazinyl)-ethyl]-2-oxazolidinone and the mixture is heated under reflux for 24 hours. Then the mixture is evaporated under reduced pressure and the residue taken up in ethyl acetate. The organic phase is washed with water, dried over magnesium sulphate and evaporated under reduced pressure. The residue is dissolved in benzene and filtered through a column filled with 100 g of aluminium oxide (activity stage II). The eluate is evaporated and, for the purpose of further purification, chromatographed on 75 g of silicagel (0.2-0.5 mm), elution being effected with a 1:1 mixture of chloroform saturated with concentrated ammonia/carbon tetrachloride. The purified product is recrystallised from ethyl acetate/petroleum ether. There is obtained 3-[2-[4-{10,11-dihydro-2-dimethylsulphamoyl-dibenzo[b,f]thiepin-10-yl}-1-piperazinyl]-ethyl]-2-oxazolidinone which melts at 164°-165° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 24 hours
  3. customThen the mixture is evaporated under reduced pressure
  4. washThe organic phase is washed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated under reduced pressure
  7. dissolutionThe residue is dissolved in benzene
  8. filtrationfiltered through a column
  9. additionfilled with 100 g of aluminium oxide (activity stage II)
  10. customThe eluate is evaporated and, for the purpose of further purification
  11. customchromatographed on 75 g of silicagel (0.2-0.5 mm), elution
  12. additionbeing effected with a 1:1 mixture of chloroform saturated with concentrated ammonia/carbon tetrachloride
  13. customThe purified product is recrystallised from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-7e5b5f3626c74bcea0cb90522e4e4c86
Source dataset
uspto-grants-1977_02
Patent number
US04006144

Reaction notes

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