GB1585027A - N-(2-(3,4-dialkoxyphenyl)ethyl)-3,4-dialkoxyphenyl-acetamides - Google Patents
N-(2-(3,4-dialkoxyphenyl)ethyl)-3,4-dialkoxyphenyl-acetamides Download PDFInfo
- Publication number
- GB1585027A GB1585027A GB3832179A GB3832179A GB1585027A GB 1585027 A GB1585027 A GB 1585027A GB 3832179 A GB3832179 A GB 3832179A GB 3832179 A GB3832179 A GB 3832179A GB 1585027 A GB1585027 A GB 1585027A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- formula
- compound
- dialkoxyphenyl
- propoxyphenyl
- 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
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
(54) N-[2-(3 ,4-DIA LKOXYPHENYL)ETHYL] -3,4
DIALKOXYPHENYLACETAMIDES
(71) We, LABORATOIRES SOCIO SA, a French company of Immeuble
Perisud, 4 rue Francois Ory, (9 2128)-Montrouge, France, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:- This invention relates to a class of amides which are useful as intermediates for preparing hydrogenated benzylisoquinoline derivatives which possess spasmolytic and hypotensive activity.
British Patent Specification No. 15582/78 (Serial No. 1,585,026) discloses compounds of formula (II), or a pharmaceutically acceptable acid addition salt thereof:
wherein R' and R2 are different and one represents a C1-C6 alkyl group and the other represents a C3-C8 alkyl group; and A and B either both represent hydrogen or together represent a covalent bond.
The compounds of formula (II) may be prepared by a process which comprises (a) cyclisation of a compound of formula (IV):
with a condensing agent (to produce a compound of formula (II) in which A and B together represent a bond); and (b) optionally reducing the resultant product (to produce a compound of formula (II) in which A and B are both hydrogen).
The present invention provides an amide of formula (IV) wherein R' and R2 are as defined with respect to formula (II) above, with the proviso that, when one of
R1 and R2 is propyl, the other is not C1-C3 alkyl.
The groups R' and R2 may be, for example ethyl, n- or iso-propyl, or n-, iso-, sec- or tert-butyl, subject to the foregoing proviso. Preferably, one of R1 and R2 represents isopropyl.
The compounds according to this invention may be prepared by known methods for preparing amides, for example by reacting a phenylethylamine of formula (V) with a compound of formula (VI):
wherein Y represents a carboxylic acid group or an ester thereof, preferably an ethyl ester and R' and R2 are as defined as above. This reaction is conveniently carried out without solvent at a temperature of from 1200-2100C.
The compounds of the present invention may be prepared by analogy with the following Examples:
Example I n-[2-(3,4-diethoxyphenyl)ethyl]-3,4-diisopropoxyphenyl acetamide
A mixture of 2 - (3,4 - diethoxyphenyl) - ethylamine (40.7 g), 0.195 mole) and ethyl 3,4 - diisopropoxyphenyl - acetate (55.7 g, 0.195 mole) was heated with stirring at 1600C for 20 hours, allowed to cool and the resulting oil taken up in 700 ml of chloroform. The organic solution was washed 3 times with 100 ml of N hydrochloric acid and then with water to pH 7. The chloroform solution was dried over magnesium sulphate, the solvent removed under reduced pressure and purification effected by chromatography over silica gel. 64.5 g (yield 72 /,,) of product was obtained sufficiently pure to be used in step (b) below.
By recrystallisation of a sample of cyclohexane N- [2(3,4 - diethoxyphenyl)ethyl] - 3,4- diisopropoxyphenyl- acetamide is obtained, m.p.=870C.
Analysis C26H3,NOs=443.6 CV0 H /n NV0 Calculated 70.40 8.41 3.16
Found 70.49 8.22 3.13
Example 2
N- [2-(3,4-Diisopropoxyphenyl)ethyl] -3 ,4-diethoxyphenyl-acetamide
N - [2 - (3,4 - Diisopropoxyphenyl)ethyl] - 3,4 - diethoxyphenylacetamide was prepared starting from 2 - (3,4 - diisopropoxyphenyl)ethylamine and ethyl 3,4 - diethoxyphenyl acetate using the process described in Example 1.
Yield=67%, m.p. 710C.
Analysis C26H37NOs=443.6 HV0 H% NV0 Calculated 70.40 8.41 3.16
Found 70.73 8.09 3.07
Example 3
N-[2-(3,4-diethoxyphenyl)ethyl]-3,4-di-n-propoxyphenylacetamide
N - [2 - (3,4 - diethoxyphenyl)ethyl - 3,4 - di - n - propoxyphenylacetamide was prepared from 2 - (3,4 - diethoxyphenyl)ethylamine and ethyl 3,4 - di - n propoxyphenyl acetate using the process described in Example 1.
Yield=77.5%, m.p. 990C
Analysis C26H37NOs=443.6 C /n 11% NV Calculated 70.40 8.41 3.16
Found 70.20 8.37 3.20
Example 4 N-[2-(3,4-di-n-propoxyphenyl)ethyl]-3,4-diethoxyphenylacetamide N - [2 - (3,4 - di - n - propoxyphenyl)ethyl] - 3,4 - diethoxyphenylacetamide was prepared from 2 - (3,4 - di - n - propoxyphenyl)ethylamine and ethyl 3,4 diethoxyphenylacetate using the process described in Example 1.
WHAT WE CLAIM IS:
1. An amide of formula (IV):
wherein R' and R2 are different and one represents a C1-C6 alkyl group and the other represents a C3-C6 alkyl group, with the proviso that, when one of R' and R2 is propyl, the other is not C13 alkyl.
2. A compound as claimed in claim 1 wherein either R' or R2 represents isopropyl.
3. A process for the preparation of a compound as claimed in claim 1, which process comprises reacting a phenylethylamine of formula (V) with a compound of formula (VI):
wherein Y represents a carboxylic acid group or an ester thereof, and R' and R2 are as defined in claim 1.
4. A process as claimed in claim 8 wherein Y represents ethoxycarbonyl.
5. A compound according to claim 1 whenever prepared by a process as claimed in claim 3 or 4.
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (5)
1. An amide of formula (IV):
wherein R' and R2 are different and one represents a C1-C6 alkyl group and the other represents a C3-C6 alkyl group, with the proviso that, when one of R' and R2 is propyl, the other is not C13 alkyl.
2. A compound as claimed in claim 1 wherein either R' or R2 represents isopropyl.
3. A process for the preparation of a compound as claimed in claim 1, which process comprises reacting a phenylethylamine of formula (V) with a compound of formula (VI):
wherein Y represents a carboxylic acid group or an ester thereof, and R' and R2 are as defined in claim 1.
4. A process as claimed in claim 8 wherein Y represents ethoxycarbonyl.
5. A compound according to claim 1 whenever prepared by a process as claimed in claim 3 or 4.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3832179A GB1585027A (en) | 1978-04-20 | 1978-04-20 | N-(2-(3,4-dialkoxyphenyl)ethyl)-3,4-dialkoxyphenyl-acetamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3832179A GB1585027A (en) | 1978-04-20 | 1978-04-20 | N-(2-(3,4-dialkoxyphenyl)ethyl)-3,4-dialkoxyphenyl-acetamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1585027A true GB1585027A (en) | 1981-02-18 |
Family
ID=10402712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3832179A Expired GB1585027A (en) | 1978-04-20 | 1978-04-20 | N-(2-(3,4-dialkoxyphenyl)ethyl)-3,4-dialkoxyphenyl-acetamides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1585027A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0178381A2 (en) * | 1984-05-29 | 1986-04-23 | Usv Pharmaceutical Corporation | Phenylacetamides as anti-allergy, anti-asthma and anti-inflammatory agents |
| WO2013078413A1 (en) * | 2011-11-22 | 2013-05-30 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Modulators of lipid storage |
-
1978
- 1978-04-20 GB GB3832179A patent/GB1585027A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0178381A2 (en) * | 1984-05-29 | 1986-04-23 | Usv Pharmaceutical Corporation | Phenylacetamides as anti-allergy, anti-asthma and anti-inflammatory agents |
| EP0178381A3 (en) * | 1984-05-29 | 1987-03-18 | Usv Pharmaceutical Corporation | Phenylacetamides as anti-allergy, anti-asthma and anti-inflammatory agents |
| WO2013078413A1 (en) * | 2011-11-22 | 2013-05-30 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Modulators of lipid storage |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19940420 |