Sodium Iodide → 3-[2-{4-[2-Chloro-10,11-dihydro-dibenz[b,f]oxepin-10-yl]-1-piperazinyl}-ethyl]-2-oxazolidinone

HRID 372430Notes

Reaction equation

HRID 372430 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[O:6][C:7]3[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=3[CH:9]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[CH2:10][C:4]=2[CH:3]=1.Cl[CH2:24][CH2:25][N:26]1[CH2:30][CH2:29][O:28][C:27]1=[O:31].C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(O)CCC>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[O:6][C:7]3[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=3[CH:9]([N:11]3[CH2:12][CH2:13][N:14]([CH2:24][CH2:25][N:26]4[CH2:30][CH2:29][O:28][C:27]4=[O:31])[CH2:15][CH2:16]3)[CH2:10][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 756333-(2-Chloroethyl)-1,3-oxazolidin-2-oneHCID 227679431-[2-Chloro-10,11-dihydro-dibenz[b,f]oxepin-10-yl]-piperazine

Product 1

HCID 203151283-[2-{4-[2-Chloro-10,11-dihydro-dibenz[b,f]oxepin-10-yl]-1-piperazinyl}-ethyl]-2-oxazolidinone

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

8.5 G. of 1-[2-chloro-10,11-dihydro-dibenz[b,f]oxepin-10-yl]-piperazine are stirred at reflux for 4 hours together with 8.1 g. of 3-(2-chloro-ethyl)-2-oxazolidinone, 2.95 g. of sodium carbonate and 0.4 g. of sodium iodide in 50 ml. of butanol. Then, the solvent is evaporated under reduced pressure and the residue partitioned between water and chloroform. The organic phase is washed with water, dried over sodium sulfate and evaporated under reduced pressure. The residue is recrystallized from methanol, and there is obtained 3-[2-{4-[2-chloro-10,11-dihydro-dibenz[b,f]oxepin-10-yl]-1-piperazinyl}-ethyl]-2-oxazolidinone having a melting point of 159°-160° C. The maleate, prepared in acetone, melts at 175°-177° C. (with decomposition). The dihydrochloride hydrate, prepared in ethanol, melts at 179°-181° C. (with decomposition).

Workup

  1. temperatureat reflux for 4 hours together with 8.1 g
  2. customThen, the solvent is evaporated under reduced pressure
  3. customthe residue partitioned between water and chloroform
  4. washThe organic phase is washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-8c60f3d9ab7d49f18f2d4810b3c71141
Source dataset
uspto-grants-1978_05
Patent number
US04091023

Reaction notes

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