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 441986Notes

Reaction equation

HRID 441986 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-methyl-dibenzo[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 100 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 precripitate, 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 dihydrochloric 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 precripitate, which is formed
  6. filtrationis filtered
  7. dry with materialThe benzene phase is dried over sodium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-9f3cd22094574d0a9ab2bb2a13ef4231
Source dataset
uspto-grants-1977_08
Patent number
US04044010

Reaction notes

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