Oxalic Acid → HCID 3041580, compound

HRID 1075825Notes

Reaction equation

HRID 1075825 reaction equation
[CH3:1][C:2]1[CH:25]=[CH:24][C:5]2[S:6][C:7]3[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][C:8]=3[C:9]([N:11]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[CH:3]=1.[BH4-].[Na+].C(O)(=O)C(O)=O>COCCOCCOC>[CH3:1][C:2]1[CH:25]=[CH:24][C:5]2[S:6][C:7]3[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][C:8]=3[CH:9]([N:11]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)[CH2:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 4311764Sodium borohydrideHCID 21541244HCID 21541244, compound

Product 1

HCID 3041580HCID 3041580, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent2×

Procedure

16 G. of 1-{2-methyl-8-(methylthio)-dibenzo[b,f]thiepin-10-yl}-4-methylpiperazine are dissolved in 200 ml. of diglyme and, at room temperature under an atmosphere of nitrogen, treated with 11.5 g. of sodium borohydride. The reaction mixture is stirred for 30 minutes and the within 45 minutes treated with a solution of 60 g. of oxalic acid in 300 ml. of diglyme. Subsequently, the mixture is heated for 2 hours at 100°, evaporated under reduced pressure and equilibrated between 2N aqueous sodium hydroxide and chloroform. The chloroform extracts are washed with water, dried and purified on a column containing 300 g. of aluminum oxide (activity grade II). 1-{10,11-dihydro-2-methyl-8-(methylthio)dibenzo[b,f]thiepin-10-yl}-4-methylpiperazine is obtained as a light oil. The corresponding maleate is precipitated from acetone and melts at 193°-194°.

Workup

  1. additionthe within 45 minutes treated with a solution of 60 g
  2. temperatureSubsequently, the mixture is heated for 2 hours at 100°
  3. customevaporated under reduced pressure
  4. washThe chloroform extracts are washed with water
  5. customdried
  6. custompurified on a column
  7. additioncontaining 300 g

Sources & evidence

ORD record
ord-1ab91f0bf40046a08721e13d417c832e
Source dataset
uspto-grants-1976_05
Patent number
US03954769

Reaction notes

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