10-Chloro-8-fluoro-10,11-dihydro-2-methyldibenzo[b,f]thiepin → HCID 21492758, compound

HRID 1973095Notes

Reaction equation

HRID 1973095 reaction equation
Cl[CH:2]1[C:8]2[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:7]=2[S:6][C:5]2[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:4]=2[CH2:3]1.[CH2:19]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[C:20]#[CH:21]>C(Cl)(Cl)Cl>[F:13][C:10]1[CH:11]=[CH:12][C:7]2[S:6][C:5]3[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:4]=3[CH2:3][CH:2]([N:25]3[CH2:26][CH2:27][N:22]([CH2:19][C:20]#[CH:21])[CH2:23][CH2:24]3)[C:8]=2[CH:9]=1

Participants

4

Reactant 2

HCID 1227554310-Chloro-8-fluoro-10,11-dihydro-2-methyldibenzo[b,f]thiepinHCID 146273691-(2-Propynyl)piperazine

Product 1

HCID 21492758HCID 21492758, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

7 G. of 10-chloro-8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]thiepin are heated under reflux for 20 hours with 7.8 g. of N-(2-propynyl)-piperazine and 40 ml. of chloroform. The chloroform is removed by evaporation and the residue is treated with ether and aqueous sodium hydroxide solution and mixed well. The ether phase is acidified with ethanolic hydrochloric acid. The precipitate which forms is removed by filtration, made alkaline with aqueous sodium hydroxide solution and taken up in benzene. The benzene phase is dried over sodium sulfate, evaporated, and there is obtained 1-[8-fluoro-10,11-dihydro-2-methyl-dibenzo[b,f]-thiepin-10-yl]-4-(2-propynyl)-piperazine which is converted into the dihydrochloride by reaction with ethanolic hydrogen chloride. The dihydrochloride melts at 230°-231° C.

Workup

  1. temperatureunder reflux for 20 hours with 7.8 g
  2. customThe chloroform is removed by evaporation
  3. additionthe residue is treated with ether and aqueous sodium hydroxide solution
  4. additionmixed well
  5. customThe precipitate which forms is removed by filtration
  6. dry with materialThe benzene phase is dried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-c123b430de154e798f882386966acfbe
Source dataset
uspto-grants-1976_12
Patent number
US03996229

Reaction notes

Loading…