SE338778B - - Google Patents
Info
- Publication number
- SE338778B SE338778B SE649668A SE649668A SE338778B SE 338778 B SE338778 B SE 338778B SE 649668 A SE649668 A SE 649668A SE 649668 A SE649668 A SE 649668A SE 338778 B SE338778 B SE 338778B
- Authority
- SE
- Sweden
- Prior art keywords
- trifluoromethyl
- give
- phenylthio
- dibenz
- dihydro
- Prior art date
Links
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 2
- 150000004885 piperazines Chemical class 0.000 abstract 2
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- FYWFCRHZXORPFH-UHFFFAOYSA-N (2-sulfanylphenyl)methanol Chemical compound OCC1=CC=CC=C1S FYWFCRHZXORPFH-UHFFFAOYSA-N 0.000 abstract 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- FDVYMJWMWMGNPA-UHFFFAOYSA-N 1-(chloromethyl)-2-[4-(trifluoromethyl)phenyl]sulfanylbenzene Chemical compound FC(C1=CC=C(C=C1)SC1=C(CCl)C=CC=C1)(F)F FDVYMJWMWMGNPA-UHFFFAOYSA-N 0.000 abstract 1
- XLQSXGGDTHANLN-UHFFFAOYSA-N 1-bromo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Br)C=C1 XLQSXGGDTHANLN-UHFFFAOYSA-N 0.000 abstract 1
- -1 2-(4-trifluoromethyl-phenylthio) benzyl Chemical group 0.000 abstract 1
- MBVVWIKWEHKYGF-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]sulfanylacetic acid Chemical compound OC(=O)CSC1=CC=C(C(F)(F)F)C=C1 MBVVWIKWEHKYGF-UHFFFAOYSA-N 0.000 abstract 1
- KMRDYEXILDUKMI-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]sulfanylacetonitrile Chemical compound FC(F)(F)C1=CC=C(SCC#N)C=C1 KMRDYEXILDUKMI-UHFFFAOYSA-N 0.000 abstract 1
- USVZHTBPMMSRHY-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-chlorophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Cl USVZHTBPMMSRHY-UHFFFAOYSA-N 0.000 abstract 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 abstract 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- 239000001110 calcium chloride Substances 0.000 abstract 1
- 229910001628 calcium chloride Inorganic materials 0.000 abstract 1
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000004678 hydrides Chemical class 0.000 abstract 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (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.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS348567 | 1967-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SE338778B true SE338778B (en) | 1971-09-20 |
Family
ID=5375059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE649668A SE338778B (en) | 1967-05-15 | 1968-05-14 |
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)
| 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 |
-
1968
- 1968-05-09 CH CH690568A patent/CH491953A/en not_active IP Right Cessation
- 1968-05-13 BE BE715070D patent/BE715070A/xx unknown
- 1968-05-13 DE DE19681770401 patent/DE1770401A1/en active Pending
- 1968-05-13 GB GB2254868A patent/GB1213912A/en not_active Expired
- 1968-05-14 FI FI134668A patent/FI55510C/en active
- 1968-05-14 SE SE649668A patent/SE338778B/xx unknown
- 1968-05-14 AT AT463368A patent/AT276405B/en active
- 1968-05-15 FR FR1566933D patent/FR1566933A/fr not_active Expired
- 1968-05-15 DK DK225068A patent/DK130074B/en unknown
- 1968-05-15 NL NL6806883A patent/NL6806883A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI55510C (en) | 1979-08-10 |
| BE715070A (en) | 1968-09-30 |
| DK130074C (en) | 1975-05-26 |
| FI55510B (en) | 1979-04-30 |
| GB1213912A (en) | 1970-11-25 |
| DE1770401A1 (en) | 1972-02-10 |
| DK130074B (en) | 1974-12-16 |
| NL6806883A (en) | 1968-11-18 |
| AT276405B (en) | 1969-11-25 |
| CH491953A (en) | 1970-06-15 |
| FR1566933A (en) | 1969-05-09 |
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