3-[2-(1-Piperazinyl)ethyl]-2-oxazolidinone → HCID 21416103, compound

HRID 1075887Notes

Reaction equation

HRID 1075887 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[S:6][C:7]3[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:8]=3[CH:9](Cl)[CH2:10][C:4]=2[CH: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>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[S:6][C:7]3[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:8]=3[CH:9]([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)[CH2:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 122755453-[2-(1-Piperazinyl)ethyl]-2-oxazolidinoneHCID 21416161HCID 21416161, compound

Product 1

HCID 21416103HCID 21416103, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

20 G. of 2,10-dichloro-10,11-dihydro-7-methyl-dibenzo[b,f]thiepin are stirred with 41 g. of 3-[2-(1-piperazinyl)-ethyl]-2-oxazolidinone and 400 ml. of chloroform at the boiling temperature for 20 hours. The solution is cooled and washed successively with 2N sodium hydroxide and with water. The organic phase is decanted and extracted with dilute methanesulfonic acid. The acid solution is made alkaline with sodium hydroxide and the oil which separates out is shaken out with ether. The ether solution is washed with water, dried over magnesium sulfate and evaporated under reduced pressure, whereby there is obtained 3-{2-[4-(2-chloro-10,11-dihydro-7-methyl-dibenzo[b,f]-thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone (melting point 161°-163°C.) which is converted into the corresponding dimethanesulfonate (melting point 187°-189°C.) by reaction with methanesulfonic acid.

Workup

  1. temperatureThe solution is cooled
  2. washwashed successively with 2N sodium hydroxide and with water
  3. customThe organic phase is decanted
  4. extractionextracted with dilute methanesulfonic acid
  5. washThe ether solution is washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9e26b0294f6d4908ac27494e540edfa1
Source dataset
uspto-grants-1976_05
Patent number
US03954764

Reaction notes

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