US2185219A - Furfuryl n-morpholine alkyl halide medicinal preparation - Google Patents
Furfuryl n-morpholine alkyl halide medicinal preparation Download PDFInfo
- Publication number
- US2185219A US2185219A US136527A US13652737A US2185219A US 2185219 A US2185219 A US 2185219A US 136527 A US136527 A US 136527A US 13652737 A US13652737 A US 13652737A US 2185219 A US2185219 A US 2185219A
- Authority
- US
- United States
- Prior art keywords
- furfuryl
- amine
- medicinal preparation
- methyl
- morpholine
- 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 - Lifetime
Links
- 238000002360 preparation method Methods 0.000 title description 20
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 14
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 13
- 150000001412 amines Chemical group 0.000 description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 235000019253 formic acid Nutrition 0.000 description 8
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 210000001002 parasympathetic nervous system Anatomy 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 5
- -1 alkyl ammonium halide Chemical class 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 150000001350 alkyl halides Chemical class 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 230000000638 stimulation Effects 0.000 description 4
- ZQSLNSHMUQXSQJ-UHFFFAOYSA-N 2-(furan-2-yl)ethanamine Chemical compound NCCC1=CC=CO1 ZQSLNSHMUQXSQJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 238000006547 Leuckart Thiophenol synthesis reaction Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical class [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Definitions
- This invention relates to a medicinal preparation and more icularly to one adapted for oral or parenteral introduction into the human system to eflect a stimulation of the para-sympathetic nervous system.
- the medicinal preparation in accordance with this invention active on the para-sympathetic nervous system, will produce variously a cathartic action, a lowering of the blo pressure, etc.
- the medicinal preparation in accordance with this invention will be a solid of high stability and of high solubility in water. ministered to the human system orally, in tablet form, or parenterally, in aqueous solution.
- the medicinal preparation in accordance with this invention comprises a quaternary furiuryl alkyl ammonium halide. More specifically, the preparation in accordance with this invention may comprise a quaternary difurfuryl alkyl aonium halide, or again, specifically, a quaternary furfuryl N-morpholine alkyl halide.
- the medicinal preparation in accordance with this invention may, for example, be an iodide, a bromide or a chloride.
- the alkyl group may be methyl, ethyl, propyl, isopropyl, butyl, amyl, or the like.
- R. is an alkyl group, as methyl, ethyl, propyl, isopropyl, butyi, amyl, or the like
- X is a halide, as iodine, bromine, chlorine, and the like.
- R is an alkyl group, as methyl, ethyl, propyl, isopropyl, butyl, amyl, or the like
- X is a halide, as iodine, bromine, chlorine, or the like.
- quaternary furfuryl trimethyl iodide may be used by introduction orally, in tablet form, or parenterally in aqueous solution with advantageous result.
- the medicinal preparation in accordance with this invention variously may be prepared in any suitable manner.
- a tertiary furfuryl ammonium compound is first prepared and then reacted with an alkyl halide to yield a salt of the quaternary amine.
- the tertiary furfuryl amines may be prepared by the use of the Leuckart synthesis known to those skilled in the art and which involves the use of an aldehyde, or a ketone and a formate of an amine, or ammonia, or the formyl compound derived by dehydration of an amine for- 25 mate.
- the production of the preparation in accordance with this invention may be accomplished by the use of furfural and the for-mates of, ror example, methyl amine, dimethyl amine, and morpholine, yielding, respectively, furfuryl methyl amine and difurfuryl methyl amine, furfuryl dlmethyl amine and furiuryl N-morpholine amine.
- the two bases obtained by this procedure are furfuryl methyl amine, boiling at 145-150" C., and difurfuryl methyl amine, boiling at 237-238 C.
- the formic acid used in the above reaction functions to react with the dimethyl amine liberated in the reaction.
- the final distillate obtained is unchanged dimethyl amide of formic acid, formic acid and furfuryl dimethyl amine.
- the furfuryl dimethyl amine is separated as described above with reference to the separation of furfuryl methyl amine; i. e. by steam distillation from acid solution and then from alkaline solution, treating the distillate with caustic soda to render it strongly alkaline, extracting the amine with ether, drying and distilling.
- the furfuryl dimethyl amine boils over the same range as the mono methyl derivative, 145-150 C.
- Furfuryl morpholine amine may be made up in the manner described above, using 5 moles of morpholine and 5 moles of formic acid and reacting with one mole of furfural.
- the tertiary amine is dissolved in dry benzene andv to the solution is added one equivalent of an alkyl halide with inducement of crystallization of the quaternary salt as, for example, by scratching the side of the vessel containing the reaction mix, or seeding with a small quantity of the crystalline quaternary salt.
- the quaternary salt will separate out in pure form after a' shorter or longer period, depending on the alkyl halide used.
- the medicinal preparation prepared in accordance with this invention will be found to possess excellent therapeutic properties, more particularly with respect to the para-sympathetic nervous system.
- the preparation is a salt of high stability and high water solubility and lends itself to introduction into the human system orally, for example, in tablet form, or parenterally in aqueous solution.
- R is an alkyl group from the group consisting of methyl, ethyl, propyl, isopropyl
- a medicinal preparation for efiecting stimulation of the para-sympathetic nervous system comprising a furfuryl N-morpholine alkyl-halide having the following formula:
- R is an alkyl group from the group consisting of methyl, ethyl, propyl, isopropyl, butyl and amyl groups.
- a medicinal preparation for efiecting stimulation of the para-sympathetic nervous system comprising furfuryl N-morpholine methiodide.
Description
aienie .li iifi ATENT YL N-MORPHOLINE ALKYL HALIDE MEDICINAL PREPARATION in Drawing. Application April 13, rear, Serial No. 136,527
3 Claims.
This invention relates to a medicinal preparation and more icularly to one adapted for oral or parenteral introduction into the human system to eflect a stimulation of the para-sympathetic nervous system. variously, the medicinal preparation in accordance with this invention, active on the para-sympathetic nervous system, will produce variously a cathartic action, a lowering of the blo pressure, etc.
The medicinal preparation in accordance with this invention will be a solid of high stability and of high solubility in water. ministered to the human system orally, in tablet form, or parenterally, in aqueous solution.
Broadly speaking, the medicinal preparation in accordance with this invention comprises a quaternary furiuryl alkyl ammonium halide. More specifically, the preparation in accordance with this invention may comprise a quaternary difurfuryl alkyl aonium halide, or again, specifically, a quaternary furfuryl N-morpholine alkyl halide.
The medicinal preparation in accordance with this invention may, for example, be an iodide, a bromide or a chloride. The alkyl group may be methyl, ethyl, propyl, isopropyl, butyl, amyl, or the like. n
From the broad standpoint, the medicinal preparation in accordance with this invention will have the following formula:
in which R. is an alkyl group, as methyl, ethyl, propyl, isopropyl, butyi, amyl, or the like, and in which X is a halide, as iodine, bromine, chlorine, and the like.
The preparation more specifically in the form of a difurfuryl alkvl =1 w onium halide will have the following iormula:
It may be ad-' in which R is an alkyl group, as methyl, ethyl, propyl, isopropyl, butyl, amyl, or the like, and X is a halide, as iodine, bromine, chlorine, or the like.
By way of example of a specific preparation in accordance with this invention which has been found to be of desirable therapeutic value and, more particularly, as a stimulator for the parasympathetic nervous system, for example, quaternary furfuryl trimethyl iodide may be used by introduction orally, in tablet form, or parenterally in aqueous solution with advantageous result.
The medicinal preparation in accordance with this invention variously may be prepared in any suitable manner. Generally speaking, a tertiary furfuryl ammonium compound is first prepared and then reacted with an alkyl halide to yield a salt of the quaternary amine.
The tertiary furfuryl amines may be prepared by the use of the Leuckart synthesis known to those skilled in the art and which involves the use of an aldehyde, or a ketone and a formate of an amine, or ammonia, or the formyl compound derived by dehydration of an amine for- 25 mate.
The production of the preparation in accordance with this invention may be accomplished by the use of furfural and the for-mates of, ror example, methyl amine, dimethyl amine, and morpholine, yielding, respectively, furfuryl methyl amine and difurfuryl methyl amine, furfuryl dlmethyl amine and furiuryl N-morpholine amine.
By way oi example of the preparation of difurfuryl methyl amine, 3 moles of methyl amine to 3 moles of formic acid in water are distilled until the temperature of the distillate reaches C. Then 2 moles of furfural are added slowly over a period of one hour, with the distillation ofi of water as it forms in the reaction. Carbon dioxide and methyl amine are also produced during the reaction, which takes place in two stages, as follows:
i l e CHO+CKaN-CHO CHa-N-OHa-l-CO:
0 Furiuml Formyl methyl Formyl lurlnryl methyl a ns min ami 1$1510 on i L -C CH N-CH CO Q CHO+ 0 OHr I o ao I Diiuriuryl methyl amine After the Iurfural has all been added and the reaction has subsided, the residue is cooled, diluted with water, made strongly alkaline and distilled until all volatile substances are removed. The distillate is then made acid with formic acid and distilled with steam as long as non-basic substances are carried over by the steam. The residue is then made strongly basic with caustic soda and the volatile amines again distilled with steam. The distillate is then treated with strong alkali and then extracted with ether to extract the mixture of bases. The extract is dried by the addition of caustic potash, the ether removed and the residual amines separated by distillation.
The two bases obtained by this procedure are furfuryl methyl amine, boiling at 145-150" C., and difurfuryl methyl amine, boiling at 237-238 C.
For production of the furfuryl dimethyl amines, moles of dimethyl amine to 5 moles of formic acid and water are distilled to 135 C. to distill oil the water. To the remaining liquid, consisting for the most part of the formyl derivative of dimethyl amine, 1 mole of furfural mixed with 1 mole of formic acid is added with heating, the temperature being maintained at 150-170 C. until the reaction is complete. The reaction mix is then distilled into a receiver. The course of this reaction may be illustrated as follows:
CH3 CH CH:
The formic acid used in the above reaction functions to react with the dimethyl amine liberated in the reaction.
The final distillate obtained is unchanged dimethyl amide of formic acid, formic acid and furfuryl dimethyl amine. The furfuryl dimethyl amine is separated as described above with reference to the separation of furfuryl methyl amine; i. e. by steam distillation from acid solution and then from alkaline solution, treating the distillate with caustic soda to render it strongly alkaline, extracting the amine with ether, drying and distilling. The furfuryl dimethyl amine boils over the same range as the mono methyl derivative, 145-150 C.
Furfuryl morpholine amine may be made up in the manner described above, using 5 moles of morpholine and 5 moles of formic acid and reacting with one mole of furfural.
In carrying out the reaction and separating the final product the procedure described above is followed.
For the preparation of the quaternary compounds, the tertiary amine is dissolved in dry benzene andv to the solution is added one equivalent of an alkyl halide with inducement of crystallization of the quaternary salt as, for example, by scratching the side of the vessel containing the reaction mix, or seeding with a small quantity of the crystalline quaternary salt.
Where pure amine and pure alkyl halide in dry benzene are used, the quaternary salt will separate out in pure form after a' shorter or longer period, depending on the alkyl halide used.
As has been indicated above, the medicinal preparation prepared in accordance with this invention will be found to possess excellent therapeutic properties, more particularly with respect to the para-sympathetic nervous system. The preparation is a salt of high stability and high water solubility and lends itself to introduction into the human system orally, for example, in tablet form, or parenterally in aqueous solution.
What I claim and desire to protect by Letters Patent is:
1. A medicinal preparation for effecting stimulation of the para-sympathetic nervous system comprising a furfuryl N-morpholine alkyl-halide having the following formula:
in which R is an alkyl group from the group consisting of methyl, ethyl, propyl, isopropyl,
, butyl and amyl groups and X is a halide.
2. A medicinal preparation for efiecting stimulation of the para-sympathetic nervous system comprising a furfuryl N-morpholine alkyl-halide having the following formula:
in which R is an alkyl group from the group consisting of methyl, ethyl, propyl, isopropyl, butyl and amyl groups.
3. A medicinal preparation for efiecting stimulation of the para-sympathetic nervous system comprising furfuryl N-morpholine methiodide.
FRED P. NABENHAUER.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US136527A US2185219A (en) | 1937-04-13 | 1937-04-13 | Furfuryl n-morpholine alkyl halide medicinal preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US136527A US2185219A (en) | 1937-04-13 | 1937-04-13 | Furfuryl n-morpholine alkyl halide medicinal preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2185219A true US2185219A (en) | 1940-01-02 |
Family
ID=22473222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US136527A Expired - Lifetime US2185219A (en) | 1937-04-13 | 1937-04-13 | Furfuryl n-morpholine alkyl halide medicinal preparation |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2185219A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3247203A (en) * | 1962-02-22 | 1966-04-19 | Aec Chim Organ Biolog | Caffeine acetyl tryptophanate |
-
1937
- 1937-04-13 US US136527A patent/US2185219A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3247203A (en) * | 1962-02-22 | 1966-04-19 | Aec Chim Organ Biolog | Caffeine acetyl tryptophanate |
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