Oxalic Acid → 1-Carbethoxy-4-(8-chloro-10,11-dihydro-2-methyl-dibenzo[b,f]-thiepin-10-yl)piperazine
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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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 evapoated 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
- additionThe reaction mixture is then mixed dropwise at 20°-30° over a 45-minute period with a solution of 138.6 g
- temperatureThe reaction mixture is maintained at 100° for 15 hours
- extractionof 2N aqueous sodium hydroxide and extracted with benzene
- extractionThe benzene extract
- washis washed with water
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-5637fac3acbf4e3ab9e455deca715454
- Source dataset
- uspto-grants-1977_08
- Patent number
- US04044010
Reaction notes
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