Oxalic acid dihydrate → 3-[2-[4-(2-Chloro-10,11-dihydro-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl]-2-oxazolidinone

HRID 435724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 435724
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[S:6][C:7]3[CH:28]=[CH:27][CH:26]=[CH:25][C:8]=3[C:9]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]4[CH2:23][CH2:22][O:21][C:20]4=[O:24])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[CH:3]=1.[BH4-].[Na+].O.O.C(O)(=O)C(O)=O>COCCOCCOC>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[S:6][C:7]3[CH:28]=[CH:27][CH:26]=[CH:25][C:8]=3[CH:9]([N:11]3[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][N:19]4[CH2:23][CH2:22][O:21][C:20]4=[O:24])[CH2:15][CH2:16]3)[CH2:10][C:4]=2[CH:3]=1

Komponenten

5

Edukt 3

HCID 61373Oxalic acid dihydrateHCID 4311764Sodium borohydrideHCID 214560453-[2-[4-(2-Chloro-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl]-2-oxazolidinone

Produkt 1

HCID 214811413-[2-[4-(2-Chloro-10,11-dihydro-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl]-2-oxazolidinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8150DiglymeLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

750 mg of 3-[2-[4-(2-chloro-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl]-2-oxazolidinone, 0.6 g of sodium borohydride and 30 ml of diglyme are treated dropwise under an argon atmosphere at 20°-30° C over a period of 15 minutes with 2.7 g of oxalic acid dihydrate in 15 ml of diglyme. The mixture is heated for 4 hours at an internal temperature of 100° C and subsequently evaporated under reduced pressure. The residue is treated with chloroform and 2-N sodium hydroxide solution. After equilibration, the aqueous phase is separated and washed twice with chloroform. The combined chloroform extracts are washed with water, dried over potassium carbonate and active carbon, filtered and evaporated under reduced pressure. There is obtained 3-[2-[4-(2-chloro-10,11-dihydro-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl]-2-oxazolidinone in the form of a brown oil. The maleate of melting point 173°-175° C is prepared by treatment with maleic acid in ethanol/ether.

Aufarbeitung

  1. customsubsequently evaporated under reduced pressure
  2. additionThe residue is treated with chloroform and 2-N sodium hydroxide solution
  3. customAfter equilibration, the aqueous phase is separated
  4. washwashed twice with chloroform
  5. washThe combined chloroform extracts are washed with water
  6. dry with materialdried over potassium carbonate and active carbon
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2db3ff3144d143a19b85f40c0efbfb36
Quelldatensatz
uspto-grants-1977_02
Patentnummer
US04006144

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