10-Chloro-8-fluoro-10,11-dihydro-2-methyldibenzo[b,f]thiepin → 2-Oxazolidinone, 3-(2-(4-(8-fluoro-2-methyl-10,11-dihydrodibenzo(b,f)thiepin-10-yl)-1-piperazinyl)ethyl)-, (+-)-

HRID 1075869Notes

Reaction equation

HRID 1075869 reaction equation
Cl[CH:2]1[C:8]2[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:7]=2[S:6][C:5]2[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:4]=2[CH2:3]1.[N:19]1([CH2:25][CH2:26][N:27]2[CH2:31][CH2:30][O:29][C:28]2=[O:32])[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>C(Cl)(Cl)Cl>[F:13][C:10]1[CH:11]=[CH:12][C:7]2[S:6][C:5]3[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:4]=3[CH2:3][CH:2]([N:22]3[CH2:23][CH2:24][N:19]([CH2:25][CH2:26][N:27]4[CH2:31][CH2:30][O:29][C:28]4=[O:32])[CH2:20][CH2:21]3)[C:8]=2[CH:9]=1

Participants

4

Reactant 2

HCID 1227554310-Chloro-8-fluoro-10,11-dihydro-2-methyldibenzo[b,f]thiepinHCID 122755453-[2-(1-Piperazinyl)ethyl]-2-oxazolidinone

Product 1

HCID 30425092-Oxazolidinone, 3-(2-(4-(8-fluoro-2-methyl-10,11-dihydrodibenzo(b,f)thiepin-10-yl)-1-piperazinyl)ethyl)-, (+-)-

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

17.6 g of 10-chloro-8-fluoro-10,11-dihydro-2-methyldibenzo[b,f]thiepin are heated for 20 hours under reflux conditions together with 27.3 g of 3-[2-(1-piperazinyl)-ethyl] -2-oxazolidinone in 10 ml of chloroform. After evaporation of the chloroform, the residue is mixed with ice, benzene and aqueous sodium hydroxide solution and again mixed well. The benzene phase is acidified with 6 N aqueous hydrochloric acid and maintained in an ice bath for 30 minutes. The precipitate, which is formed, is filtered, made alkaline with aqueous sodium hydroxide solution and taken up in benzene. The benzene phase is dried over sodium sulphate and evaporated, whereby 3-{2-[4-(8-fluoro-10,11-dihydro-2-methyl-dibenzo [b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone is obtained, which is converted into the corresponding dihydrochloride by reaction with ethanolic hydrochloric acid. The dihydrochloride melts at 210°(dec;).

Workup

  1. customAfter evaporation of the chloroform
  2. additionthe residue is mixed with ice, benzene and aqueous sodium hydroxide solution
  3. additionagain mixed well
  4. temperaturemaintained in an ice bath for 30 minutes
  5. customThe precipitate, which is formed
  6. filtrationis filtered
  7. dry with materialThe benzene phase is dried over sodium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-a1e411f230ff4e519b765c0055edae80
Source dataset
uspto-grants-1976_05
Patent number
US03954764

Reaction notes

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