CS200149B1 - Substituted n-/4(phenoxy)butyl/piperidines and method of their preparing - Google Patents
Substituted n-/4(phenoxy)butyl/piperidines and method of their preparing Download PDFInfo
- Publication number
- CS200149B1 CS200149B1 CS36479A CS36479A CS200149B1 CS 200149 B1 CS200149 B1 CS 200149B1 CS 36479 A CS36479 A CS 36479A CS 36479 A CS36479 A CS 36479A CS 200149 B1 CS200149 B1 CS 200149B1
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- CS
- Czechoslovakia
- Prior art keywords
- butyl
- substituted
- tert
- piperidines
- phenoxy
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 13
- 150000003053 piperidines Chemical class 0.000 title description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- -1 methoxy, n-butyl Chemical group 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- XLDXCWGOXWMBAX-UHFFFAOYSA-N 1-(4-phenoxybutyl)piperidine Chemical class C=1C=CC=CC=1OCCCCN1CCCCC1 XLDXCWGOXWMBAX-UHFFFAOYSA-N 0.000 claims description 2
- QBLISOIWPZSVIK-UHFFFAOYSA-N 4-bromobutoxybenzene Chemical class BrCCCCOC1=CC=CC=C1 QBLISOIWPZSVIK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 description 7
- 239000002168 alkylating agent Substances 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 7
- CHHNKCNFDJFXSP-UHFFFAOYSA-N 1-(4-bromobutoxy)-2-methylbenzene Chemical compound CC1=CC=CC=C1OCCCCBr CHHNKCNFDJFXSP-UHFFFAOYSA-N 0.000 description 1
- HMIRHFRURCHFGW-UHFFFAOYSA-N 1-(4-bromobutoxy)-3-methoxybenzene Chemical compound COC1=CC=CC(OCCCCBr)=C1 HMIRHFRURCHFGW-UHFFFAOYSA-N 0.000 description 1
- XUXTYMRIRSWKQT-UHFFFAOYSA-N 1-(4-bromobutoxy)-4-butylbenzene Chemical compound CCCCC1=CC=C(OCCCCBr)C=C1 XUXTYMRIRSWKQT-UHFFFAOYSA-N 0.000 description 1
- DPTVPYBSBNIACI-UHFFFAOYSA-N 1-(4-bromobutoxy)-4-chlorobenzene Chemical compound ClC1=CC=C(OCCCCBr)C=C1 DPTVPYBSBNIACI-UHFFFAOYSA-N 0.000 description 1
- PIJXSPIZKQDHEL-UHFFFAOYSA-N 1-(4-bromobutoxy)-4-nonylbenzene Chemical compound CCCCCCCCCC1=CC=C(OCCCCBr)C=C1 PIJXSPIZKQDHEL-UHFFFAOYSA-N 0.000 description 1
- AHTOPYJXJBLILF-UHFFFAOYSA-N 1-[4-(2-methylphenoxy)butyl]piperidine Chemical compound CC1=CC=CC=C1OCCCCN1CCCCC1 AHTOPYJXJBLILF-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 230000001670 myorelaxant effect Effects 0.000 description 1
- 125000004351 phenylcyclohexyl group Chemical group C1(=CC=CC=C1)C1(CCCCC1)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
Description
Vynález sa týká substituovaných N-(4-(fenoxy)butyl) piperiďínov obecného vzorcaThe invention relates to substituted N- (4- (phenoxy) butyl) piperidines of the general formula
R krfe R značí: orto- metyl, metoxy, n-butyl, sec.butyl, terč.butyl, fenyl eyklohexyl; meta- metoxy; para- ttwtyl, metoxy, n-butyl, sec.butyl, terč.butyl, fenyl, eyklohexyl, terc.oktyl, n-nonyl a chlór, a spAeobu ich pripravy. Ako je zháme, niektoré deriváty piperidínu vykazujú biologické vlastnosti, ako napr. hypotenzívny, lokálně anestetický, myorelaxačný, antiadrenolytický účinok apod.. Zlúčeniny, ktoré eú podstatou vynálezu, však eéte připravené neboli a sú nové, v literatúre neoplsané. Slúžia ako. východiskové látky pri príprave dalSlch biologicky aktivnych zlúčenin.R @ 1 denotes: ortho-methyl, methoxy, n-butyl, sec-butyl, tert-butyl, phenyl cyclohexyl; methoxy; paratthyl, methoxy, n-butyl, sec-butyl, tert-butyl, phenyl, cyclohexyl, tert-octyl, n-nonyl and chlorine, and methods for their preparation. As noted above, some piperidine derivatives exhibit biological properties, such as e.g. hypotensive, locally anesthetic, myorelaxant, antiadrenolytic effect, etc. However, the compounds of the present invention have not been prepared yet and are novel and not disclosed in the literature. They serve as. starting materials in the preparation of other biologically active compounds.
Nové zlúčeniny sa pripravujú spčsobom podía vynálezu, ktorého podstatou je, že reaguje eubstituoýaný l-bróm-4-fenoxybután /význam substltuentov jo ten istý ako vySie/ 8 piperidlnom v prostředí vriacoho benzénu počas 6 hodin. SpAsob podía vynálezu dává vysoké výtažky, čisté produkty a pracovný postup je jednoduchý.The novel compounds are prepared by the process of the invention, which comprises reacting the substituted 1-bromo-4-phenoxybutane (meaning substituents as above) with piperidine in boiling benzene for 6 hours. The process of the invention gives high yields, clean products and the process is simple.
Na ilustráciu sp&sobu pripravy ako i niektorých fyzikálnych vlastnosti sú uvedené následovně příklady.To illustrate the preparation process as well as some physical properties, the following examples are given.
200 149200 149
200 140200 140
Příklad 1Example 1
Za varu sa k 0,2 mol piperidinu rozpuštěného v 150 ml benzénu přidá 0,1 mol l-bróm-4-o-metylfenoxybutánu a nechá sa reagovat 6 hodin. Po ochladení a odfiltrováni reakčnej zmesi aa rozpú&ťadlo oddestiluje a produkt sa predestiluje. N-/4-(o-metylfenoxy)-butyl/piperidin vzniká vo výťažku 77 %·, t.v. 143 až 145 °C/0,08 kPa, elementárna analýza (vypočítané/ nájdené X): 0=77,68/77,71, H=10,19/10,22, N=5,66/5,49.While boiling, 0.1 mol of 1-bromo-4-o-methylphenoxybutane is added to 0.2 mol of piperidine dissolved in 150 ml of benzene and allowed to react for 6 hours. After cooling and filtering off the reaction mixture, the solvent was distilled off and the product was distilled off. N- (4- (o-methylphenoxy) butyl) piperidine is obtained in 77% yield, b.p. 143-145 ° C / 0.08 kPa, elemental analysis (calculated / found X): 0 = 77.68 / 77.71, H = 10.19 / 10.22, N = 5.66 / 5.49.
Příklad 2Example 2
Pracovný postup je ten istý ako v přiklade 1, ako alkylačné činidlo sa v&ak použil l-bróm-4-m-metoxyfenoxybután. Výťažok produktu je 69 %, t.v. 157 až 157,5 °C/0,05 kPa, elementárna analýza (vypočítané/nájdené X): 0=72,97/73,03, H=9,57/9,50, N=5,32/5,41.The procedure is the same as in Example 1 except that 1-bromo-4-m-methoxyphenoxybutane was used as the alkylating agent. The product yield is 69%, b.p. 157-157.5 ° C / 0.05 kPa, elemental analysis (calculated / found X): 0 = 72.97 / 73.03, H = 9.57 / 9.50, N = 5.32 / 5, 41st
Přiklad 3Example 3
Pracovný postup je ten istý ako v přiklade 1, ako alkylačná činidlo sa použil 1-brám-4-p-n-butylfenoxybután. Výťažok produktu je 68 X, t.v. 153 °C/0,03 kPa, η^θ=1,5093, elemen tárna analýza (vypočítaná/nájdené X): 0=78,84/78,90, H=10,79/10,91, 1(=4,84/5,00, -\ax= >225,279,285 nm.The procedure is the same as in Example 1, using 1-bromo-4-p-butylphenoxybutane as the alkylating agent. The yield of the product is 68%, t 153 ° C / 0.03 kPa, η 1 = 1.5093, elemental analysis (calculated / found X): 0 = 78.84 / 78.90, H = 10.79 / 10.91.1 (= 4.84 / 5.00, - \ ax => 225.279.285 nm).
««
Přiklad 4Example 4
Pracovný postup je ten istý ako v přiklade 1, ako alkylačné činidlo sa však použil l-bróm-4-o-sec.butylfenoxybut&n. Výťažok produktu je 56 %, t.v. 140 °C/0,04 kPa, n^°=l,5096 elementárna analýza (vypočltané/nájdené X): 0=78,84/78,75, H=10,79/10,71, N=4,84/4,80, /^^^=221,276 nm.The procedure is the same as in Example 1, but 1-bromo-4-o-sec-butylphenoxybutene was used as the alkylating agent. The product yield is 56%, b.p. 140 ° C / 0.04 kPa, n 1 ° = 1.5096 elemental analysis (calculated / found X): 0 = 78.84 / 78.75, H = 10.79 / 10.71, N = 4.84 [.Alpha.] D @ 20 = 221.276 nm.
Příklad 5Example 5
Pracovný postup je ten istý ako v příklade 1, ako alkylačné činidlo sa použil 1-brdm-4-p-terc.butylfenoxybután. Výťažok produktu je 82 X, t.v. 162 °C/0,08 kPa, ηρ°=1,5128, ele mentárna analýza (vypočítané/nájdené X): 0=78,84/78,69, H=10,79/10,87, N=4,84/4,93,ΛΒβχ= 225,279 nm.The procedure is the same as in Example 1, using 1-brdm-4-p-tert-butylphenoxybutane as the alkylating agent. The product yield is 82%, t 162 ° C / 0.08 kPa, ηρ ° = 1.5128, electronic analysis (calculated / found X): 0 = 78.84 / 78.69, H = 10.79 / 10 , 87, N = 4.84 / 4.93, Λβχ = 225.279 nm.
Příklad 6Example 6
Pracovný postup je ten istý ako v příklade 1, ako alkylačné činidlo sa použil 1-brdm-4-o-fenylfenoxybután. Výťažok produktu je 82 X, t.v. 186 až 190 °C/0,03 kPa, elementárna analýza (vypočítané/nájdené X): 0=81,51/81.73, H=8,79/8,90, N«4,53/4,47.The procedure is the same as in Example 1, using 1-brdm-4-o-phenylphenoxybutane as the alkylating agent. The product yield is 82%, b.p. 186-190 ° C / 0.03 kPa, elemental analysis (calculated / found X): δ = 81.51 / 81.73, H = 8.79 / 8.90, N 4,5 4.53 / 4.47.
Přiklad 7Example 7
Pracovný postup je ten istý ako v přiklade 1, ako alkylačné činidlo sa použil 1-bróm-4-p-chldrfenoxybután. Výťažok produktu je 71 X, t.v. 156 až 158 °C/0,08 kPa, elementárna analýza (vypočítané/nájdené X): 0=67,33/67,19, H=8,29/8,22, N=5,23/5,44.The procedure is the same as in Example 1, using 1-bromo-4-p-chlorophenoxybutane as the alkylating agent. The product yield is 71%, b.p. 156-158 ° C / 0.08 kPa, elemental analysis (calculated / found X): 0 = 67.33 / 67.19, H = 8.29 / 8.22, N = 5.23 / 5.44.
Příklad 8Example 8
Pracovný postup je ten istý ako v příklade 1, ako alkyla£né činidlo sa použil 1-bróm-4-p-n-nonylfenoxybután. Výťažok produktu je 67 %, t.v. 182 až 185 °C/0,03 kPa, elementárna analýza (vypočítané/nójdené %): 0=80,16/80,06, H«ll,49/11,55, R=3,91/4,03.The procedure is the same as in Example 1, using 1-bromo-4-p-n-nonylphenoxybutane as the alkylating agent. The product yield is 67%, b.p. M.p. 182-185 ° C / 0.03 kPa, elemental analysis (calculated / found%): 0 = 80.16 / 80.06, H 11, 49 / 11.55, R = 3.91 / 4.03.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS36479A CS200149B1 (en) | 1979-01-17 | 1979-01-17 | Substituted n-/4(phenoxy)butyl/piperidines and method of their preparing |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS36479A CS200149B1 (en) | 1979-01-17 | 1979-01-17 | Substituted n-/4(phenoxy)butyl/piperidines and method of their preparing |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS200149B1 true CS200149B1 (en) | 1980-08-29 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS36479A CS200149B1 (en) | 1979-01-17 | 1979-01-17 | Substituted n-/4(phenoxy)butyl/piperidines and method of their preparing |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS200149B1 (en) |
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1979
- 1979-01-17 CS CS36479A patent/CS200149B1/en unknown
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