CA1042463A - Tertiary-alkylamino-lower acyl-xylidides - Google Patents
Tertiary-alkylamino-lower acyl-xylididesInfo
- Publication number
- CA1042463A CA1042463A CA000287278A CA287278A CA1042463A CA 1042463 A CA1042463 A CA 1042463A CA 000287278 A CA000287278 A CA 000287278A CA 287278 A CA287278 A CA 287278A CA 1042463 A CA1042463 A CA 1042463A
- Authority
- CA
- Canada
- Prior art keywords
- tert
- acetoxylidide
- amylamino
- compound
- process according
- 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
Abstract
ABSTRACT OF THE DISCLOSURE
The invention is the compound 2-(N-tert.amylamino)-2',6'-acetoxylidide and its acid addition salts. The compound is a useful inter-mediate in the production of 2-(N-ethyl-tert. amylamino)-2',6'-acetoxylidine and 2-(N-n-propyl tert.amylamino)-2',6'-acetoxylidide, which are useful local anaesthetics having long lasting effects.
The invention is the compound 2-(N-tert.amylamino)-2',6'-acetoxylidide and its acid addition salts. The compound is a useful inter-mediate in the production of 2-(N-ethyl-tert. amylamino)-2',6'-acetoxylidine and 2-(N-n-propyl tert.amylamino)-2',6'-acetoxylidide, which are useful local anaesthetics having long lasting effects.
Description
This application is a divisiona] of our copending Canadian patent application Serial No. 164,740, filed February 27~ 1973.
This application Telates to the compound 2-~N-tert.amylamino)-
This application Telates to the compound 2-~N-tert.amylamino)-
2',6'-acetoxylidide.
Our copending Canadian patent application Serial No. 164,740 relates to 2-(N-ethyl-tert.amylamino)-2',6'-acetoxylidide and 2-~N-n-propyl-tert.-amylamino)-2',6'-acetoxylidide, their pharmaceutically acceptable salts and their use as local anaesthetics. -This invention relates to a novel compound which is a useful intermediate in the production of the compounds which are the subject of our application Serial No. 164,740. The novel compound is 2-~N-tert.-amylamino)-2',6'-acetoxylidide, of the formula .
CH, \ 1 3 The invention also relates to the acid addition salts of the compound.
The compound 2-(N-tert. amylamino)-2',6'-acetoxylidide can be prepared by reacting a compound of formula ~ NH-C-CH~-X
in which X is chlorine, bromine or iodine, with tert. amylamine.
~hen X is chlorine or bromine the reaction is preferably carried out in the presence of an alkali metal iodide, for example, sodium iodide or potassium iodide or a quaternary ammonium iodide.
The compound 2-(N-ter~.-amylamino)-2',6'-acetoxylidide can be reacted with an alkylating agent to ob~ain 2-(N-ethyl.tert~ amylamino)-2',6'-acetoxylidide of 2-~N~n-propyl-tert.amylamino)-2'~6'-acetoxylidide in accor-dance with our copending application Serial No. 164~740.
The invention is ~urther illustrated in the following Example showing the preparation of 2-(N-tert.amylamino)-21~6~-aeetoxylidide.
To 400 ml of anhydrous benzene, 18.9 g (0.09S6 mole) 2-chloro-2l~6t-acetoxylidide~ 20 g (0.2295 mole) tert.amylamine and 1 g. of sodium iodide were added. The reaction mixture was heated at 100C for 36 hours in an autoclave. A precipitate was collected and discardedO The resulting filtrate was stripped of solvent and the yellow oily residue was dissolved in ether, the undissolved material being collected and discarded~ After drying (Na2S04) the ether was stripped off in vacuo leaving a yellow oily liquid which was taken up in dilute hydrochloric acid (~inal pH 2)c The acidic aqueous phase was washed several times with ether, basified to pH
9.5 with concentrated ammonia, and the preeipitated base extracted with ether (4xlO0 ml3. The ether extract was dried (Na2S04) and evaporated n vacuo leaving a yellow oily residue which was distilled in vacuo (b.p.
150C., 0.02 mm.) to give under refrigeration, 16.6 g. of a white solid~
m~p. 54-55.5C~ (The hydrochloride was also prepared and recrystallized from acetonitrile, m.p. 209-211C.) Anal. Caled. for C15H24N20: C~ 72-54; H~ 9-74; N~ 28-Found: C, 72032; H, 9.98; N~ 11.34c I.r, (~Br disc~ hydrochloride) 3150-3120 (m-s; amide, NH streteh); 2710 (s), 2620 (m)~ 2580 (m~ 2440 (m~ and 2417 (m-w) (NH+ streteh)/ .1665 (s; amide I). 1590 (m-w; aromatic~ 1542 (S3 amide II), 1393 and 1375 (s-m; methyl CH bending), 775 (s~m; 3 adjacent out of plane aromatic H) cm 1.
:
Our copending Canadian patent application Serial No. 164,740 relates to 2-(N-ethyl-tert.amylamino)-2',6'-acetoxylidide and 2-~N-n-propyl-tert.-amylamino)-2',6'-acetoxylidide, their pharmaceutically acceptable salts and their use as local anaesthetics. -This invention relates to a novel compound which is a useful intermediate in the production of the compounds which are the subject of our application Serial No. 164,740. The novel compound is 2-~N-tert.-amylamino)-2',6'-acetoxylidide, of the formula .
CH, \ 1 3 The invention also relates to the acid addition salts of the compound.
The compound 2-(N-tert. amylamino)-2',6'-acetoxylidide can be prepared by reacting a compound of formula ~ NH-C-CH~-X
in which X is chlorine, bromine or iodine, with tert. amylamine.
~hen X is chlorine or bromine the reaction is preferably carried out in the presence of an alkali metal iodide, for example, sodium iodide or potassium iodide or a quaternary ammonium iodide.
The compound 2-(N-ter~.-amylamino)-2',6'-acetoxylidide can be reacted with an alkylating agent to ob~ain 2-(N-ethyl.tert~ amylamino)-2',6'-acetoxylidide of 2-~N~n-propyl-tert.amylamino)-2'~6'-acetoxylidide in accor-dance with our copending application Serial No. 164~740.
The invention is ~urther illustrated in the following Example showing the preparation of 2-(N-tert.amylamino)-21~6~-aeetoxylidide.
To 400 ml of anhydrous benzene, 18.9 g (0.09S6 mole) 2-chloro-2l~6t-acetoxylidide~ 20 g (0.2295 mole) tert.amylamine and 1 g. of sodium iodide were added. The reaction mixture was heated at 100C for 36 hours in an autoclave. A precipitate was collected and discardedO The resulting filtrate was stripped of solvent and the yellow oily residue was dissolved in ether, the undissolved material being collected and discarded~ After drying (Na2S04) the ether was stripped off in vacuo leaving a yellow oily liquid which was taken up in dilute hydrochloric acid (~inal pH 2)c The acidic aqueous phase was washed several times with ether, basified to pH
9.5 with concentrated ammonia, and the preeipitated base extracted with ether (4xlO0 ml3. The ether extract was dried (Na2S04) and evaporated n vacuo leaving a yellow oily residue which was distilled in vacuo (b.p.
150C., 0.02 mm.) to give under refrigeration, 16.6 g. of a white solid~
m~p. 54-55.5C~ (The hydrochloride was also prepared and recrystallized from acetonitrile, m.p. 209-211C.) Anal. Caled. for C15H24N20: C~ 72-54; H~ 9-74; N~ 28-Found: C, 72032; H, 9.98; N~ 11.34c I.r, (~Br disc~ hydrochloride) 3150-3120 (m-s; amide, NH streteh); 2710 (s), 2620 (m)~ 2580 (m~ 2440 (m~ and 2417 (m-w) (NH+ streteh)/ .1665 (s; amide I). 1590 (m-w; aromatic~ 1542 (S3 amide II), 1393 and 1375 (s-m; methyl CH bending), 775 (s~m; 3 adjacent out of plane aromatic H) cm 1.
:
Claims (6)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A process for preparing the compound 2-(N-tert.amylamino)-2', 6'-acetoxylidide of formula which comprises reacting a compound of formula in which X is chlorine, bromine or iodine, with tert.-amylamine, and if de-sired converting the product into an acid addition salt.
2. A process according to claim 1 wherein X is chlorine or bromine the reaction is carried out in the presence of an alkali metal iodide or a quaternary ammonium iodide.
3. A process according to claim 2 wherein 2-chloro-2',6'-acetoxyl-idide is reacted with tert.-amylamine in the presence of sodium iodide.
4. A process according to claim 3 wherein the product of the reaction between 2-chloro-2',6'-acetoxylidide and tert.amylamine is reacted with hydrogen chloride to obtain the hydrochloride salt.
5. The compound 2-(N-tert.-amylamino)-2',6'-acetoxylidide when made by a process according to claim 1 or by an obvious chemical equivalent thereof.
6. The compound 2-(N-tert.-amylamino)-2',6'-acetoxylidide hydro-chloride when made by a process according to claim 4 or by an obvious chemi-cal equivalent thereof.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23011472A | 1972-02-28 | 1972-02-28 | |
| US32537873A | 1973-01-22 | 1973-01-22 | |
| AT587374A AT326641B (en) | 1972-02-28 | 1973-02-26 | PROCESS FOR THE PREPARATION OF NEW N, N-DIALKYLAMINOACETIC ACID-2,6-XYLIDIDES |
| CA164,740A CA1023765A (en) | 1973-01-22 | 1973-02-27 | Tertiary-alkylamino-lower acyl-xylidides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1042463A true CA1042463A (en) | 1978-11-14 |
Family
ID=30773541
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000287278A Expired CA1042463A (en) | 1972-02-28 | 1977-09-22 | Tertiary-alkylamino-lower acyl-xylidides |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1042463A (en) |
-
1977
- 1977-09-22 CA CA000287278A patent/CA1042463A/en not_active Expired
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