GB1213912A - Tricyclic piperazine derivatives and a method of preparing same - Google Patents

Tricyclic piperazine derivatives and a method of preparing same

Info

Publication number
GB1213912A
GB1213912A GB2254868A GB2254868A GB1213912A GB 1213912 A GB1213912 A GB 1213912A GB 2254868 A GB2254868 A GB 2254868A GB 2254868 A GB2254868 A GB 2254868A GB 1213912 A GB1213912 A GB 1213912A
Authority
GB
United Kingdom
Prior art keywords
trifluoromethyl
give
phenylthio
dibenz
dihydro
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB2254868A
Inventor
Miroslav Protiva
Karel Pelz
Jiri Jilek
Vera Seidlova
Jirina Metysova
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Spofa Vereinigte Pharma Werke
Original Assignee
Spofa Vereinigte Pharma Werke
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Spofa Vereinigte Pharma Werke filed Critical Spofa Vereinigte Pharma Werke
Publication of GB1213912A publication Critical patent/GB1213912A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
    • C07D313/02—Seven-membered rings
    • C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
    • C07D313/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
    • C07D313/14—[b,f]-condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
    • C07D337/02—Seven-membered rings
    • C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
    • C07D337/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
    • C07D337/14—[b,f]-condensed

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1,213,912. Tricyclic piperazine derivatives. SPOFA, UNITED PHARMACEUTICAL WORKS. 13 May, 1968 [15 May, 1967], No. 22548/68. Heading C2C. Novel tricyclic piperazine derivatives of formula wherein X stands for an atom of sulphur or oxygen, and R for a halogen atom, a C 1-4 alkyl group or trifluoromethyl group or a salt thereof, are prepared by condensing a chloroderivative of formula wherein X and R are as defined above, with 1- carbethoxy-piperazine so as to form the carbamate of formula wherein X and R are as defined above; reducing the carbamate with a complex hydride and when the salt is to be prepared neutralizing the base thus formed with an inorganic or organic acid to the corresponding salt. 8 - Trifluoromethyl - 10 - chloro - 10,11 - dihydro-dibenz[b,f]-thiopine is prepared by reaction of 4-trifluoromethyl-bromobenzene with 2- hydroxymethyl-thiophenol to give 2-(4-trifluoromethyl-phenylthio) benzyl alcohol, reacting this with thionyl chloride to give 2-(4-trifluoromethyl-phenylthio) benzyl chloride, reacting this with potassium cyanide to give 2-(4-trifluoromethyl-phenylthio) - acetonitrile, reacting this with potassium hydroxide to give 2-(4- trifluoromethyl-phenylthio)- acetic acid, treating this with anhydrous hydrogen fluoride to give 8-trifluoromethyl - 10,11-dihydro-dibenz-(b,f)-thiopin-10-one, reducing this with sodium borohydride to 8-trifluoromethyl-10,11 -dihydro-dibenz- [b,f]-thiopin-10-ol, and treating this with calcium chloride and anhydrous hydrogen chloride. Reference has been directed by the Comptroller to Specifications 1,093,910 and 1,123,400.
GB2254868A 1967-05-15 1968-05-13 Tricyclic piperazine derivatives and a method of preparing same Expired GB1213912A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CS348567 1967-05-15

Publications (1)

Publication Number Publication Date
GB1213912A true GB1213912A (en) 1970-11-25

Family

ID=5375059

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2254868A Expired GB1213912A (en) 1967-05-15 1968-05-13 Tricyclic piperazine derivatives and a method of preparing same

Country Status (10)

Country Link
AT (1) AT276405B (en)
BE (1) BE715070A (en)
CH (1) CH491953A (en)
DE (1) DE1770401A1 (en)
DK (1) DK130074B (en)
FI (1) FI55510C (en)
FR (1) FR1566933A (en)
GB (1) GB1213912A (en)
NL (1) NL6806883A (en)
SE (1) SE338778B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE757868A (en) * 1969-10-25 1971-04-01 Spofa Usines Pharma Reunies PROCESS FOR PREPARATION OF NEW 10-PIPERAZINO-10,11-DIHYDRODIBENZO / B, F, / THIEPINES AND THEIR SALTS, AS WELL AS THE PRODUCTS OBTAINED

Also Published As

Publication number Publication date
AT276405B (en) 1969-11-25
DK130074C (en) 1975-05-26
SE338778B (en) 1971-09-20
DK130074B (en) 1974-12-16
FI55510B (en) 1979-04-30
NL6806883A (en) 1968-11-18
BE715070A (en) 1968-09-30
FI55510C (en) 1979-08-10
DE1770401A1 (en) 1972-02-10
CH491953A (en) 1970-06-15
FR1566933A (en) 1969-05-09

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee