Water → 1-(8-Fluoro-2-methyl-dibenzo[b,f]thiepin-10-yl)-4-methyl-piperazine
Reaction equation
[F: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][C:7](=O)[C:6]=2[CH:18]=1.[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(=O)(O)[O-].[Na+].O>C1C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[F: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:23]3[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]3)[C:6]=2[CH:18]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
18 g of 8-fluoro-2-methyl-dibenzo[b,f]thiepin-10(11H)-one in 140 ml of absolute benzene are together with 33.2 ml of N methylpiperazine within 1/2 hour at 20°-25° treated with a solution of 5.8 ml of titanium tetrachloride in 40 ml of absolute benzene. The reaction mixture is subsequently heated for 20 hours under reflux conditions. The reaction mixture is poured, with vigorous stirring, into a mixture of 40 ml of saturated aqueous sodium bicarbonate solution and 120 ml of water, subsequently filtered and extracted with chloroform. The organic phase is dried and evaporated. One obtains 1-(8-fluoro-2-methyl-dibenzo[b,f]thiepin-10-yl)-4-methyl-piperazine, which is converted into the corresponding maleate by treatment with maleic acid. The maleate melts at 244° with decomposition.
Workup
- temperatureThe reaction mixture is subsequently heated for 20 hours under reflux conditions
- filtrationsubsequently filtered
- extractionextracted with chloroform
- customThe organic phase is dried
- customevaporated
Sources & evidence
- ORD record
- ord-2bff0885b2434bb9b785c03d3cf03436
- Source dataset
- uspto-grants-1976_06
- Patent number
- US03966737
Reaction notes
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