GB765544A - Production of amides and ketones having basic substituents - Google Patents
Production of amides and ketones having basic substituentsInfo
- Publication number
- GB765544A GB765544A GB6298/55A GB629855A GB765544A GB 765544 A GB765544 A GB 765544A GB 6298/55 A GB6298/55 A GB 6298/55A GB 629855 A GB629855 A GB 629855A GB 765544 A GB765544 A GB 765544A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ketone
- alkyl
- xylidide
- starting materials
- amine
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The hydrohalide of an amide or ketone having the general formula: <FORM:0765544/IV(b)/1> wherein R is a hydrogen atom or an alkyl, aryl or aralkyl group, R1 is an aryl group or an aryl-amino group which may contain alkyl groups or halogen atoms as nuclear substituents and/or an alkyl substituent on the nitrogen atom of the amino group, R2 and R3 are both alkyl or cycloalkyl groups or together represent a polymethylene or alkyl-substituted polymethylene group, and Hal is a halogen atom, is prepared by treating an amide or ketone R.CH2.COR1 with an N-halogeno secondary amine R2.N(Hal).R3 in an inert solvent. Suitable solvents are dialkyl ethers, cyclic ethers or carbon tetrahalides. If an acid acceptor is present in the reaction the product is a free base. Acid acceptors referred to are an excess of the secondary amine, a tertiary amine and an alkali metal salt of a weak acid. Amine starting materials referred to are N-chlordimethylamine, N - chlormethylethylamine, N - chlordiethylamine, N - chlordi - n - propylamine, N - chlordi - p - butylamine, N - chloropiperidine and N-chlorodicyclohexylamine. Ketone starting materials include acetophenone, propiophenone, methyl tolyl ketone, ethyl tolyl ketone and methyl xylyl ketone, and amide starting materials include acetanilide, aceto-ortho-toluidine, acet - para - toluidide, acet - 2.4 - xylidide, acet-2,6 - xylidide, propionanilide propion - 2.4-xylidide, propion - 2.6 - xylidide, orthochloroacetanilide, para - chloroacetanilide, 2.4-, 2.5 - dichloroacetanilide and 2.4, 6 - trichloroacetanilides, para - chloropropionanilide, N - methylacetanilide and N - ethylacetanilide. Examples describe the preparation of 2.6-dimethyl - N.N. - diethyl glycylanilide, 2.5 - di - chloro - N.N. - di - n - propyl alanylanilide, a -piperidinopropiophenone hydrochloride and a -dimethylaminodesoxybenzoin. Starting materials. N-Halogeno secondary amines are prepared from the appropriate secondary amine and a cold aqueous solution of an alkali metal hypohalite, preferably in the presence of a solvent for the amine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL765544X | 1954-03-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB765544A true GB765544A (en) | 1957-01-09 |
Family
ID=11056276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6298/55A Expired GB765544A (en) | 1954-03-03 | 1955-03-03 | Production of amides and ketones having basic substituents |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB765544A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3287217A (en) * | 1966-11-22 | Compositions and methods for stimulat- ing the central nervous system and in- creasing the blood pressure | ||
| US3305562A (en) * | 1960-05-24 | 1967-02-21 | Wander Ag Dr A | Process for making alpha-pyrrolidino-valerophenones |
| US3314970A (en) * | 1967-04-18 | Pykrolidino ketones |
-
1955
- 1955-03-03 GB GB6298/55A patent/GB765544A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3287217A (en) * | 1966-11-22 | Compositions and methods for stimulat- ing the central nervous system and in- creasing the blood pressure | ||
| US3314970A (en) * | 1967-04-18 | Pykrolidino ketones | ||
| US3305562A (en) * | 1960-05-24 | 1967-02-21 | Wander Ag Dr A | Process for making alpha-pyrrolidino-valerophenones |
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