GB847051A - Novel pentane derivatives and a process for the manufacture thereof - Google Patents
Novel pentane derivatives and a process for the manufacture thereofInfo
- Publication number
- GB847051A GB847051A GB23707/58A GB2370758A GB847051A GB 847051 A GB847051 A GB 847051A GB 23707/58 A GB23707/58 A GB 23707/58A GB 2370758 A GB2370758 A GB 2370758A GB 847051 A GB847051 A GB 847051A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pentanol
- treatment
- methyl
- manufacture
- raney
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
- 239000007868 Raney catalyst Substances 0.000 abstract 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 2
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- -1 methoxy phenyl Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- XLKNMWIXNFVJRR-UHFFFAOYSA-N boron potassium Chemical compound [B].[K] XLKNMWIXNFVJRR-UHFFFAOYSA-N 0.000 abstract 1
- 125000002091 cationic group Chemical group 0.000 abstract 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- 229940102396 methyl bromide Drugs 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229940075930 picrate Drugs 0.000 abstract 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 abstract 1
Classifications
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- 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
Abstract
The invention comprises esters of the general formula :- <FORM:0847051/IV(b)/1> and acid addition salts thereof wherein R is a phenyl or naphthyl or a nitro and/or a methoxy phenyl radical and a process for the manufacture thereof whereby 5-(11-methyl-piperidyl-41)-pentanol-2 with an appropriate benzoic or naphthoic acid halide and, if desired, converting the resulting ester hydrohalide into the free ester by treatment with a base or into a further acid addition salt by cationic exchange or treatment with a base followed by treatment with an acid. 5-(11-Methyl-piperidyl-41)-pentanol-2 and its hydro-bromide is prepared by reacting 4-vinyl-pyridine with sodio ethyl acetoacetate to give ethyl 2 - acetyl - 4-(pyridyl-41)-butyrate (and its picrate) which is subjected to alkaline hydrolysis to give 5-(pyridyl-41)pentanone-2 this in turn is reduced to 5-(pyridye-41)-pentanol-2 (and its hydrobromide) either by lithium aluminium hydride, hydrogen in the presence of Raney-nickel, or potassium boron hydride, and the alcohol is quaturnised with methyl bromide and reduced by hydrogen and Raney-nickel.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB23707/58A GB847051A (en) | 1958-07-23 | 1958-07-23 | Novel pentane derivatives and a process for the manufacture thereof |
| BE580783A BE580783A (en) | 1958-07-23 | 1959-07-16 | Process for the preparation of methyl-piperidyl-pentanol esters. |
| ES0250984A ES250984A1 (en) | 1958-07-23 | 1959-07-22 | Novel pentane derivatives and a process for the manufacture thereof |
| FR833959A FR66M (en) | 1958-07-23 | 1960-07-26 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB23707/58A GB847051A (en) | 1958-07-23 | 1958-07-23 | Novel pentane derivatives and a process for the manufacture thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB847051A true GB847051A (en) | 1960-09-07 |
Family
ID=10199985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23707/58A Expired GB847051A (en) | 1958-07-23 | 1958-07-23 | Novel pentane derivatives and a process for the manufacture thereof |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE580783A (en) |
| ES (1) | ES250984A1 (en) |
| FR (1) | FR66M (en) |
| GB (1) | GB847051A (en) |
-
1958
- 1958-07-23 GB GB23707/58A patent/GB847051A/en not_active Expired
-
1959
- 1959-07-16 BE BE580783A patent/BE580783A/en unknown
- 1959-07-22 ES ES0250984A patent/ES250984A1/en not_active Expired
-
1960
- 1960-07-26 FR FR833959A patent/FR66M/fr active Active
Also Published As
| Publication number | Publication date |
|---|---|
| BE580783A (en) | 1960-01-18 |
| ES250984A1 (en) | 1960-01-16 |
| FR66M (en) | 1961-01-09 |
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