3-[2-(1-Piperazinyl)ethyl]-2-oxazolidinone → 3-{2-[4-(8-Fluoro-10,11-dihydro-3-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone

HRID 441996Notes

Reaction equation

HRID 441996 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]=[C:15]([CH3:18])[CH:16]=[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]=[C:15]([CH3:18])[CH:16]=[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 122755453-[2-(1-Piperazinyl)ethyl]-2-oxazolidinoneHCID 21416157HCID 21416157, compound

Product 1

HCID 214162053-{2-[4-(8-Fluoro-10,11-dihydro-3-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

10.6 g. of 10-chloro-8-fluoro-10,11-dihydro-3-methyl-dibenzo[b,f]thiepin are heated at reflux together with 200 ml. of chloroform and 22.8 g. of 3-[2-(1-piperazinyl)-ethyl]-2-oxazolidinone for 30 hours. Thereafter, the mixture is evaporated under reduced pressure, and the residue is worked up as described in Example 5. The insoluble base is recrystallized from ethanol, whereby there is obtained 3-{2-[4-(8-fluoro-10,11-dihydro-3-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone which melts at 173°-175° C. The maleate crystallizes from acetone/ether and has a melting point of 147°-149° C.

Workup

  1. temperatureat reflux together with 200 ml
  2. customThereafter, the mixture is evaporated under reduced pressure
  3. customThe insoluble base is recrystallized from ethanol

Sources & evidence

ORD record
ord-4e6cf82ac527423f930f1a9735f88cc5
Source dataset
uspto-grants-1977_08
Patent number
US04044010

Reaction notes

Loading…