GB789339A - New basic ethers and their salts, and process for the production thereof - Google Patents
New basic ethers and their salts, and process for the production thereofInfo
- Publication number
- GB789339A GB789339A GB35652/55A GB3565255A GB789339A GB 789339 A GB789339 A GB 789339A GB 35652/55 A GB35652/55 A GB 35652/55A GB 3565255 A GB3565255 A GB 3565255A GB 789339 A GB789339 A GB 789339A
- Authority
- GB
- United Kingdom
- Prior art keywords
- morpholino
- propane
- hexyloxy
- hydrochloride
- radical
- 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
- C07D295/08—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 singly bound oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0789339/IV (b)/1> (wherein A is an alkyl radical of 6 to 8 carbon atoms or an aralkyl radical of 7 or 8 carbon atoms and Y is a branched chain alkylene radical of 3 to 6 carbon atoms) and their acidaddition salts; and their preparation by (a) reacting a compound AX (X being a reactive acid radical, e.g. halogen, or a radical derived from sulphuric acid, an alkyl sulphuric acid or an alkyl- or aryl-sulphonic acid) with a metal salt of the appropriate morpholino-alkanol; or (b) reacting a metal salt of an alcohol A-OH with a compound of the formula <FORM:0789339/IV (b)/2> or an acid-addition salt thereof; or (c) reacting a compound of the formula A-O-Y-NH2 with a b : b 1-dihalogen diethyl ether, preferably in presence of acid-binding agents. In this last reaction the amine starting material may be mono- or di-benzylated. Compounds in which the radical Y is unbranched in the a -position to the morpholino group can also be obtained by reduction, e.g. with lithium aluminium hydride, of suitable alkoxy- or aralkoxy-alkyl carboxylic acid morpholides. In examples: (1) 1 - morpholino - propan - 2 - ol (obtained from propylene oxide and morpholine) and n-hexyl bromide with sodium in xylene give 1 - (41 - morpholino) - 2 - hexyloxypropane (hydrochloride described); (2) 1-benzylamino-propanol-(2) (obtained by reductive condensation of isopropanolamine and benzaldehyde) and n-hexyl bromide give 1-benzylamino-2-hexyloxy-propane, isolated as the hydrochloride, and the free base on heating with b : b 1 - dichloro - diethylether yields 1 - (41-morpholino) - 2 - hexyloxy - propane (hydrochloride described), which is also obtained by heating 1 - amino - 2 - hexyloxy - propane (obtained by hydrogenolysis of 1-benzylamino-2-hexyloxy-propane hydrochloride) with the dichloro ether; (3) 1-(41-morpholino)-propanol-(2) and thionyl chloride give 1-(41-morpholino)-2-chloropropane hydrochloride, which with n-hexanol and sodium in xylene gives 1-(41-morpholino) - 2 - hexyloxy - propane; (4) 2 - aminopropanol and n-hexyl bromide give 1-hexyloxy-2-amino-propane and this with b : b 1-dichlorodiethyl ether, with or without potash, gives 1 - hexyloxy - 2 - morpholino - propane (hydrochloride described); (5) 1-(41-morpholino)-2-hydroxy-propane and benzyl chloride give 1-(41-morpholino) - 2 - benzyloxy - propane (hydrochloride described); (6) 2 - amino - butanol-(3) (obtained by reducing the 2-nitrobutan-(3)-ol obtained from nitroethane and acetaldehyde) and n-hexyl bromide give 2-hexyloxyl-3-amino butane and this with b : b 1-dichloro-diethyl ether, with or without potash, gives 2-hexyloxy-3-(41-morpholino)-butane.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH789339X | 1955-01-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB789339A true GB789339A (en) | 1958-01-22 |
Family
ID=4536842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35652/55A Expired GB789339A (en) | 1955-01-08 | 1955-12-12 | New basic ethers and their salts, and process for the production thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB789339A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105493174A (en) * | 2013-07-05 | 2016-04-13 | 斯蒂芬·施普伦格尔 | Percussion, wind and rattling instrument and musical-instrument arrangement |
-
1955
- 1955-12-12 GB GB35652/55A patent/GB789339A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105493174A (en) * | 2013-07-05 | 2016-04-13 | 斯蒂芬·施普伦格尔 | Percussion, wind and rattling instrument and musical-instrument arrangement |
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