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

HRID 441995Notes

Reaction equation

HRID 441995 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:9]=3[CH:8]=[C:7]([N:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][N:25]4[CH2:29][CH2:28][O:27][C:26]4=[O:30])[CH2:19][CH2:18]3)[C:6]=2[CH:31]=1.[BH4-].[Na+].C(O)(=O)C(O)=O>COCCOCCOC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:9]=3[CH2:8][CH:7]([N:17]3[CH2:18][CH2:19][N:20]([CH2:23][CH2:24][N:25]4[CH2:29][CH2:28][O:27][C:26]4=[O:30])[CH2:21][CH2:22]3)[C:6]=2[CH:31]=1

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 4311764Sodium borohydrideHCID 214160983-[2-[4-(8-Chloro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl]-2-oxazolidinone

Product 1

HCID 214161293-{2-[4-(8-Chloro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent2×

Conditions

Temperature
100 °C

Procedure

1.0 G. of 3-{2-[4-(8-chloro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl}-2-oxazolidinone is stirred at room temperature with 50 ml. of diethyleneglycol dimethyl ether (diglyme) and 0.6 g. of sodium borohydride for 30 minutes under an atmosphere of argon. Thereafter, a solution of 2.8 g. of oxalic acid (C2H2O4 . 2H2 o) in 15 ml. of diglyme is added dropwise at 20°-30° C. The mixture is stirred at 100° C. for 4 hours, and subsequently evaporated under reduced pressure. The residue is taken up in 2N sodium hydroxide and water, and extracted three times with 100 ml. of benzene each time. The combined benzene phases are washed with water, dried over magnesium sulfate, filtered and concentrated. the crystalline residue is recrystallized from ethyl acetate/petroleum ether (low boiling), whereby there is obtained 3-{2-[4-(8-chloro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)-1 -piperazinyl]-ethyl}-2-oxazolidinone, having a melting point of 184°-186° C. The maleate crystallizes from methanol/ether and melts at 174°-175° C.

Workup

  1. customsubsequently evaporated under reduced pressure
  2. extractionwater, and extracted three times with 100 ml
  3. washThe combined benzene phases are washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe crystalline residue is recrystallized from ethyl acetate/petroleum ether (low boiling)

Sources & evidence

ORD record
ord-76bef12af26f461ebdafbd15d5b88359
Source dataset
uspto-grants-1977_08
Patent number
US04044010

Reaction notes

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