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1-Methylpiperazine → 3-Fluoro-8-isopropyl-10-(4-methylpiperazino)-10,11-dihydrodibenzo(b,f)thiepin

HRID 1389286
Notes
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Reaction equation

HRID 1389286 reaction equation
FC1C=CC2CC(=O)C3C=C(C(C)C)C=CC=3SC=2C=1.CN1CCNCC1.C(O)(=O)/C=C\C(O)=O.C([O-])(=O)/C=C\C([O-])=O.[F:44][C:45]1[CH:46]=[CH:47][C:48]2[CH:54]=[C:53]([N:55]3[CH2:60][CH2:59][N:58]([CH3:61])[CH2:57][CH2:56]3)[C:52]3[CH:62]=[C:63]([CH:66]([CH3:68])[CH3:67])[CH:64]=[CH:65][C:51]=3[S:50][C:49]=2[CH:69]=1>C1C=CC=CC=1.C(O)C.[Ti](Cl)(Cl)(Cl)Cl.CCOCC.O>[F:44][C:45]1[CH:46]=[CH:47][C:48]2[CH2:54][CH:53]([N:55]3[CH2:56][CH2:57][N:58]([CH3:61])[CH2:59][CH2:60]3)[C:52]3[CH:62]=[C:63]([CH:66]([CH3:67])[CH3:68])[CH:64]=[CH:65][C:51]=3[S:50][C:49]=2[CH:69]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

11

Reactant 5

HCID 531671-MethylpiperazineHCID 444266Maleic AcidHCID 8263943-fluoro-8-isopropyldibenzo(b,f)thiepin-10(11H)-oneHCID 30541753-Fluoro-8-isopropyl-10-(4-methylpiperazino)dibenzo(b,f)thiepinHCID 5288227Maleate(2-)

Product 1

HCID 3054166
3-Fluoro-8-isopropyl-10-(4-methylpiperazino)-10,11-dihydrodibenzo(b,f)thiepin

Reagents, catalysts & solvents 5

HCID 24193Titanium TetrachlorideCatalystHCID 241BenzeneSolvent3×HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A stirred solution of 8.0 g 3-fluoro-8-isopropyldibenzo(b,f)thiepin-10(11H)-one in 55 ml benzene is treated with a solution of 2.8 g titanium tetrachloride in 14 ml benzene added dropwise. 14 g of 1-methylpiperazine are then slowly added and the mixture refluxed for 16 hours. After cooling, it is decomposed with 80 ml water, added dropwise. 100 ml benzene are then added and the separated solid is filtered. The benzene layer of the filtrate is washed with water, dried with potassium carbonate and evaporated. There are obtained 9.2 g (89%) crude oily base which is neutralized with maleic acid in ethanol. Addition of ether separates the crystalline maleate of 3-fluoro-8-isopropyl-10-(4-methylpiperazino)dibenzo(b,f)thiepin melting at 183°-184° C. with decomposition (ethanol-ether).

Workup

  1. additionadded dropwise
  2. temperaturethe mixture refluxed for 16 hours
  3. temperatureAfter cooling
  4. additionadded dropwise
  5. filtrationthe separated solid is filtered
  6. washThe benzene layer of the filtrate is washed with water
  7. dry with materialdried with potassium carbonate
  8. customevaporated
  9. customThere are obtained 9.2 g (89%) crude oily base which

Sources & evidence

ORD record
ord-9185e63d697445ea99dfb04f0363baca
Source dataset
uspto-grants-1981_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04243805

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes