Oxalic Acid → 1-Carbethoxy-4-(8-chloro-10,11-dihydro-2-methyl-dibenzo[b,f]-thiepin-10-yl)piperazine

HRID 1075862Notes

Reaction equation

HRID 1075862 reaction equation
[C:1]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:18]3[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=3[S:16][C:15]3[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:14]=3[CH:13]=2)[CH2:8][CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2].[BH4-].[Na+].C(O)(=O)C(O)=O>COCCOCCOC>[C:1]([N:6]1[CH2:7][CH2:8][N:9]([CH:12]2[C:18]3[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=3[S:16][C:15]3[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:14]=3[CH2:13]2)[CH2:10][CH2:11]1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 4311764Sodium borohydrideHCID 214161321-Carbethoxy-4-(8-chloro-2-methyl-dibenzo[b,f]thiepin-10-yl)-piperazine

Product 1

HCID 214160911-Carbethoxy-4-(8-chloro-10,11-dihydro-2-methyl-dibenzo[b,f]-thiepin-10-yl)piperazine

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent2×

Procedure

41.5 G. of 1-carbethoxy-4-(8-chloro-2-methyl-dibenzo[b,f]thiepin-10-yl)piperazine are reacted together with 1 l. of absolute diglyme (diethyleneglycoldimethylether) with 26.5 g. of sodium borohydride and stirred at 25° for 30 minutes. The reaction mixture is then mixed dropwise at 20°-30° over a 45-minute period with a solution of 138.6 g. of oxalic acid in 800 ml. of diglyme. The reaction mixture is maintained at 100° for 15 hours. The resulting mixture is evaporated under reduced pressure. The residue is suspended in 1 l. of 2N aqueous sodium hydroxide and extracted with benzene. The benzene extract is washed with water, dried and evaporated, whereby there is obtained 1-carbethoxy-4-(8-chloro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin-10-yl)piperazine as a red-brown oil, whose nmr and ir spectra are consistent with the proposed structure.

Workup

  1. additionThe reaction mixture is then mixed dropwise at 20°-30° over a 45-minute period with a solution of 138.6 g
  2. temperatureThe reaction mixture is maintained at 100° for 15 hours
  3. customThe resulting mixture is evaporated under reduced pressure
  4. extractionof 2N aqueous sodium hydroxide and extracted with benzene
  5. extractionThe benzene extract
  6. washis washed with water
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-45853c4e33bb44cbb72b447a89b2cff8
Source dataset
uspto-grants-1976_05
Patent number
US03954764

Reaction notes

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