CA1210027A - Process for the preparation of 2-/e/phenyl- methylenecycloheptan-1-one-/e/-oxime - Google Patents
Process for the preparation of 2-/e/phenyl- methylenecycloheptan-1-one-/e/-oximeInfo
- Publication number
- CA1210027A CA1210027A CA000425105A CA425105A CA1210027A CA 1210027 A CA1210027 A CA 1210027A CA 000425105 A CA000425105 A CA 000425105A CA 425105 A CA425105 A CA 425105A CA 1210027 A CA1210027 A CA 1210027A
- Authority
- CA
- Canada
- Prior art keywords
- water
- ice
- alcohol
- reaction
- mixture
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 43
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- 239000012429 reaction media Substances 0.000 claims abstract description 15
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000002443 hydroxylamines Chemical class 0.000 claims abstract description 4
- 238000011065 in-situ storage Methods 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 18
- 125000001931 aliphatic group Chemical group 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 239000011541 reaction mixture Substances 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BQCRDGOBIZRDJH-ACCUITESSA-N (2e)-2-benzylidenecycloheptan-1-one Chemical compound O=C1CCCCC\C1=C/C1=CC=CC=C1 BQCRDGOBIZRDJH-ACCUITESSA-N 0.000 description 1
- SDEBYHVDMCQKNZ-UHFFFAOYSA-N 4-methoxy-6-piperazin-1-ylpyrimidine;hydrochloride Chemical compound Cl.C1=NC(OC)=CC(N2CCNCC2)=N1 SDEBYHVDMCQKNZ-UHFFFAOYSA-N 0.000 description 1
- 241001502381 Budorcas taxicolor Species 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 101100536883 Legionella pneumophila subsp. pneumophila (strain Philadelphia 1 / ATCC 33152 / DSM 7513) thi5 gene Proteins 0.000 description 1
- 241000357437 Mola Species 0.000 description 1
- 101100240664 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nmt1 gene Proteins 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- -1 hydroxylamine salts Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/15—Oximes (>C=N—O—); Hydrazines (>N—N<); Hydrazones (>N—N=) ; Imines (C—N=C)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/44—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups being part of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU997/82 | 1982-04-01 | ||
| HU82997A HU185518B (en) | 1982-04-01 | 1982-04-01 | Process for preparing 2-/e/-phenyl-methylene-cycloheptan-1-one-/e/-oxime |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1210027A true CA1210027A (en) | 1986-08-19 |
Family
ID=10952372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000425105A Expired CA1210027A (en) | 1982-04-01 | 1983-03-31 | Process for the preparation of 2-/e/phenyl- methylenecycloheptan-1-one-/e/-oxime |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS58208262A (de) |
| AT (1) | AT384423B (de) |
| BE (1) | BE896279A (de) |
| CA (1) | CA1210027A (de) |
| CH (1) | CH656121B (de) |
| DD (1) | DD209619A5 (de) |
| DE (1) | DE3311895A1 (de) |
| DK (1) | DK148783A (de) |
| ES (1) | ES521096A0 (de) |
| FI (1) | FI831087L (de) |
| FR (1) | FR2524464B1 (de) |
| GB (1) | GB2117773B (de) |
| HU (1) | HU185518B (de) |
| IL (1) | IL68079A (de) |
| IT (1) | IT1194184B (de) |
| NL (1) | NL8301175A (de) |
| SE (1) | SE8301817L (de) |
| YU (1) | YU77683A (de) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4083978A (en) * | 1976-01-27 | 1978-04-11 | Egyt Gyogyszervegyeszeti Gyar | Oxime ethers |
-
1982
- 1982-04-01 HU HU82997A patent/HU185518B/hu not_active IP Right Cessation
-
1983
- 1983-03-07 IL IL68079A patent/IL68079A/xx unknown
- 1983-03-28 BE BE1/10748A patent/BE896279A/fr not_active IP Right Cessation
- 1983-03-29 ES ES521096A patent/ES521096A0/es active Granted
- 1983-03-30 SE SE8301817A patent/SE8301817L/xx not_active Application Discontinuation
- 1983-03-30 FI FI831087A patent/FI831087L/fi not_active Application Discontinuation
- 1983-03-30 DK DK148783A patent/DK148783A/da not_active IP Right Cessation
- 1983-03-31 GB GB08308956A patent/GB2117773B/en not_active Expired
- 1983-03-31 JP JP58056809A patent/JPS58208262A/ja active Pending
- 1983-03-31 CH CH179183A patent/CH656121B/de unknown
- 1983-03-31 CA CA000425105A patent/CA1210027A/en not_active Expired
- 1983-03-31 DE DE19833311895 patent/DE3311895A1/de not_active Withdrawn
- 1983-03-31 FR FR8305314A patent/FR2524464B1/fr not_active Expired
- 1983-04-01 AT AT0116983A patent/AT384423B/de not_active IP Right Cessation
- 1983-04-01 IT IT20428/83A patent/IT1194184B/it active
- 1983-04-01 NL NL8301175A patent/NL8301175A/nl not_active Application Discontinuation
- 1983-04-01 YU YU00776/83A patent/YU77683A/xx unknown
- 1983-04-04 DD DD83249465A patent/DD209619A5/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58208262A (ja) | 1983-12-03 |
| IT1194184B (it) | 1988-09-14 |
| NL8301175A (nl) | 1983-11-01 |
| DD209619A5 (de) | 1984-05-16 |
| IT8320428A1 (it) | 1984-10-01 |
| IL68079A (en) | 1986-10-31 |
| ES8405366A1 (es) | 1984-06-01 |
| ES521096A0 (es) | 1984-06-01 |
| FR2524464B1 (fr) | 1986-05-30 |
| SE8301817L (sv) | 1983-10-02 |
| ATA116983A (de) | 1987-04-15 |
| IT8320428A0 (it) | 1983-04-01 |
| GB8308956D0 (en) | 1983-05-11 |
| AT384423B (de) | 1987-11-10 |
| CH656121B (de) | 1986-06-13 |
| HU185518B (en) | 1985-02-28 |
| BE896279A (fr) | 1983-09-28 |
| FR2524464A1 (fr) | 1983-10-07 |
| YU77683A (en) | 1985-12-31 |
| IL68079A0 (en) | 1983-06-15 |
| SE8301817D0 (sv) | 1983-03-30 |
| DE3311895A1 (de) | 1983-10-06 |
| FI831087L (fi) | 1983-10-02 |
| GB2117773A (en) | 1983-10-19 |
| DK148783A (da) | 1983-10-02 |
| GB2117773B (en) | 1985-08-29 |
| DK148783D0 (da) | 1983-03-30 |
| FI831087A0 (fi) | 1983-03-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |