DK142318B - Analogifremgangsmåde til fremstilling af piperidinoalkylphenothiaziner eller syreadditionssalte deraf. - Google Patents
Analogifremgangsmåde til fremstilling af piperidinoalkylphenothiaziner eller syreadditionssalte deraf. Download PDFInfo
- Publication number
- DK142318B DK142318B DK240672AA DK240672A DK142318B DK 142318 B DK142318 B DK 142318B DK 240672A A DK240672A A DK 240672AA DK 240672 A DK240672 A DK 240672A DK 142318 B DK142318 B DK 142318B
- Authority
- DK
- Denmark
- Prior art keywords
- propyl
- piperidino
- solution
- formula
- ether
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 28
- 150000003839 salts Chemical class 0.000 title claims description 12
- 150000002990 phenothiazines Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 cyclic acetal Chemical class 0.000 claims description 69
- 150000001875 compounds Chemical class 0.000 claims description 51
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 230000000694 effects Effects 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 235000005985 organic acids Nutrition 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 3
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000002734 organomagnesium group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Chemical group 0.000 claims 2
- MLEGMEBCXGDFQT-UHFFFAOYSA-N 1-benzylpiperidin-2-one Chemical compound O=C1CCCCN1CC1=CC=CC=C1 MLEGMEBCXGDFQT-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
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- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229940125782 compound 2 Drugs 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 209
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- 239000000243 solution Substances 0.000 description 127
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 100
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- 239000002244 precipitate Substances 0.000 description 52
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 39
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- 239000000047 product Substances 0.000 description 36
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- 241001465754 Metazoa Species 0.000 description 21
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- 230000008020 evaporation Effects 0.000 description 17
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 17
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 16
- PLDUPXSUYLZYBN-UHFFFAOYSA-N Fluphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 PLDUPXSUYLZYBN-UHFFFAOYSA-N 0.000 description 14
- 238000001035 drying Methods 0.000 description 14
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- 238000010992 reflux Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
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- 229910021529 ammonia Inorganic materials 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 230000002378 acidificating effect Effects 0.000 description 11
- 235000009518 sodium iodide Nutrition 0.000 description 11
- 239000012230 colorless oil Substances 0.000 description 10
- 235000019439 ethyl acetate Nutrition 0.000 description 10
- 229910052753 mercury Inorganic materials 0.000 description 10
- 230000000701 neuroleptic effect Effects 0.000 description 10
- 230000008485 antagonism Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 229950000688 phenothiazine Drugs 0.000 description 9
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- BZEJZIAESDBOJX-UHFFFAOYSA-N 10-(3-chloropropyl)-2-(trifluoromethyl)phenothiazine Chemical compound C1=CC=C2N(CCCCl)C3=CC(C(F)(F)F)=CC=C3SC2=C1 BZEJZIAESDBOJX-UHFFFAOYSA-N 0.000 description 7
- VAIHBHWKPBXNLR-UHFFFAOYSA-N 2-piperidin-4-yloxyethanol Chemical compound OCCOC1CCNCC1 VAIHBHWKPBXNLR-UHFFFAOYSA-N 0.000 description 7
- 235000019270 ammonium chloride Nutrition 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 7
- 230000008673 vomiting Effects 0.000 description 7
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/48—Oxygen atoms attached in position 4 having an acyclic carbon atom attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7117510A FR2137150B1 (fr) | 1971-05-14 | 1971-05-14 | |
| FR7117509 | 1971-05-14 | ||
| FR7117510 | 1971-05-14 | ||
| FR717117509A FR2137149B1 (fr) | 1971-05-14 | 1971-05-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK142318B true DK142318B (da) | 1980-10-13 |
| DK142318C DK142318C (fr) | 1981-03-02 |
Family
ID=26216390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK240672AA DK142318B (da) | 1971-05-14 | 1972-05-15 | Analogifremgangsmåde til fremstilling af piperidinoalkylphenothiaziner eller syreadditionssalte deraf. |
Country Status (13)
| Country | Link |
|---|---|
| JP (2) | JPS5118958B1 (fr) |
| AU (1) | AU461649B2 (fr) |
| BE (1) | BE783411A (fr) |
| CH (1) | CH553215A (fr) |
| DE (2) | DE2264903C3 (fr) |
| DK (1) | DK142318B (fr) |
| FI (1) | FI55657C (fr) |
| FR (2) | FR2137150B1 (fr) |
| GB (2) | GB1383773A (fr) |
| IL (1) | IL39296A (fr) |
| NL (1) | NL175824C (fr) |
| NO (1) | NO135365C (fr) |
| SE (2) | SE405973B (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0621267A1 (fr) * | 1993-04-07 | 1994-10-26 | Shell Internationale Researchmaatschappij B.V. | Dérivés de spiropipéridine et leur utilisation comme fongicides |
| US20040072825A1 (en) * | 2000-12-19 | 2004-04-15 | Yves Lamberty | 2-(2-(4-((2r)-2-methyl-3-(10h-phenothiazin-10-yl)propyl)-1-piperazinyl)-ethoxy) ethanol, process for the preparation thereof, pharmaceutical compositions containing said compound and therapeutic uses thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1344593A (fr) * | 1961-11-25 | 1963-11-29 | Boehringer & Soehne Gmbh | Procédé pour la préparation de nouveaux dérivés de l'alcoxy-pipéridine et de leurs sels |
-
1971
- 1971-05-14 FR FR7117510A patent/FR2137150B1/fr not_active Expired
- 1971-05-14 FR FR717117509A patent/FR2137149B1/fr not_active Expired
-
1972
- 1972-04-25 IL IL39296A patent/IL39296A/en unknown
- 1972-04-27 CH CH629072A patent/CH553215A/fr not_active IP Right Cessation
- 1972-05-09 SE SE7206146A patent/SE405973B/xx unknown
- 1972-05-09 FI FI1305/72A patent/FI55657C/fi active
- 1972-05-10 DE DE2264903A patent/DE2264903C3/de not_active Expired
- 1972-05-10 DE DE2222931A patent/DE2222931C3/de not_active Expired
- 1972-05-12 BE BE783411A patent/BE783411A/fr not_active IP Right Cessation
- 1972-05-12 NO NO1690/72A patent/NO135365C/no unknown
- 1972-05-12 AU AU42226/72A patent/AU461649B2/en not_active Expired
- 1972-05-13 JP JP47046917A patent/JPS5118958B1/ja active Pending
- 1972-05-15 NL NLAANVRAGE7206504,A patent/NL175824C/xx not_active IP Right Cessation
- 1972-05-15 DK DK240672AA patent/DK142318B/da not_active IP Right Cessation
- 1972-05-15 GB GB2277272A patent/GB1383773A/en not_active Expired
- 1972-05-15 GB GB3172274A patent/GB1383774A/en not_active Expired
-
1975
- 1975-05-06 SE SE7505250A patent/SE418964B/xx unknown
- 1975-11-25 JP JP50140299A patent/JPS5248988B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU461649B2 (en) | 1975-06-05 |
| DE2264903A1 (de) | 1975-08-28 |
| FI55657C (fi) | 1979-09-10 |
| NO135365C (no) | 1977-03-30 |
| IL39296A (en) | 1976-03-31 |
| DE2222931B2 (de) | 1977-11-10 |
| SE7505250L (fr) | 1975-05-06 |
| DE2264903B2 (de) | 1981-02-19 |
| NL175824B (nl) | 1984-08-01 |
| GB1383773A (en) | 1974-02-12 |
| JPS5118958B1 (fr) | 1976-06-14 |
| DE2222931A1 (de) | 1972-11-30 |
| SE405973B (sv) | 1979-01-15 |
| FR2137149A1 (fr) | 1972-12-29 |
| BE783411A (fr) | 1972-11-13 |
| DE2222931C3 (de) | 1978-07-06 |
| NO135365B (fr) | 1976-12-20 |
| FR2137150A1 (fr) | 1972-12-29 |
| FR2137150B1 (fr) | 1975-01-17 |
| JPS5248988B2 (fr) | 1977-12-14 |
| NL175824C (nl) | 1985-01-02 |
| FR2137149B1 (fr) | 1973-05-11 |
| JPS5191267A (fr) | 1976-08-10 |
| GB1383774A (en) | 1974-02-12 |
| AU4222672A (en) | 1973-12-06 |
| CH553215A (fr) | 1974-08-30 |
| FI55657B (fi) | 1979-05-31 |
| IL39296A0 (en) | 1972-06-28 |
| NL7206504A (fr) | 1972-11-16 |
| DE2264903C3 (de) | 1981-12-17 |
| SE418964B (sv) | 1981-07-06 |
| DK142318C (fr) | 1981-03-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |