IE46732B1 - N-(2-(3,4-dialkoxyphenyl)ethyl)-3,4-dialkoxyphenylacetamides - Google Patents
N-(2-(3,4-dialkoxyphenyl)ethyl)-3,4-dialkoxyphenylacetamidesInfo
- Publication number
- IE46732B1 IE46732B1 IE2296/81A IE229681A IE46732B1 IE 46732 B1 IE46732 B1 IE 46732B1 IE 2296/81 A IE2296/81 A IE 2296/81A IE 229681 A IE229681 A IE 229681A IE 46732 B1 IE46732 B1 IE 46732B1
- Authority
- IE
- Ireland
- Prior art keywords
- ethyl
- formula
- compound
- diethoxyphenyl
- dialkoxyphenylacetamides
- Prior art date
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
This invention relates to a class of amides which are useful as intermediates for preparing hydrogenated benzylisoguinoline derivatives which possess spasmolytic and hypotensive activity.
Patent Specification No. 46731 discloses compounds of formula (II), or a pharmaceutically acceptable acid addition salt thereof:
(II) 'Γ
2 wherein R and R are different and one represents a Gj.'-Gg alkyl group and the other represents a C^-Cg 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):
(IV)
OR
OR 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 1 2 formula (IV) wherein R and R are as defined with respect to formula (II) above, with the proviso that,
2 when one. of R and R is propyl, the other is not C.-C3 alkyl.
The groups R^ and R^ may be, for example ethyl, n- or iso-propyl, or η-, iso-, sec- or tert -butyl, subject to the foregoing proviso. Preferably, one of 1 2
R and R represents isopropyl.
The compounds according to this invention may be prepared by known methods for preparing amides, for example by reacting a phenylethylanine of formula (V) with a compound of formula (VI):
(VI) wherein Y represents a carboxylic acid group or an ester thereof, preferably an ethyl ester and R1 and
R are as defined as above. This reaction is conveniently carried out without solvent at a temperature of from 12O°-21O°c.
The compounds of the present invention may be prepared by analogy with the following Examples:
Example 1 n-/2-(3,4-diethoxyphenyl)ethyl7-3,4diisopropoxyphenylacetamide
A mixture of 2 - (3,4 - diethoxyphenyl) - ethylamine (40«7g), 0.195 mole) and ethyl 3,4 - diisopropoxyphenyl - acetate (55.7 g, 0.195 mole) was heated with stirring at 160°C 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) ethylj7 - 3,4 - diisopropoxyphenylacetamide is obtained, m.p.=37°C.
Analysis C2 gH, 71:0^-443.6
C% K% Calculated 70.40 8.41 3.16 Pound 70.49 8.22 3.13
Example 2
11-/2-(3,4-Diisopropoxyphenyl)ethyl/-3, 4diethoxyphenylacetamide
N - /2 - (3,4- Diisopropoxyphenyl)ethyl7 3,4 - diethoxyphenylacetamide was prepared starting from 2 - (3,4 - diisoproxyphenyi)ethylamine and ethyl 3,4 diethoxyphenyl acetate using the process described in Example 1.
Yield=67%, m.p. 71°C. Analysis ^6^37^5^43.6
C% N% 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-npropoxyphenylacetamide
N - j/ί - (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.
- 6 Yield=77.5%, m.p. 99°C
Analysis C Β,Λ=443.6 26 37 5
C% HS NS Calculated 70.40 8.41 3.16 5 Pound 70.20 8.37 3.20
Example 4
N-/2-(3,4-di-&-propoxyphenyl)ethyl/7-3,4diethoxyphenylacetamide
N-/2- (3,4 -di -n- propoxyphenyl)ethyl7 10 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.
Claims (5)
1. CLAIMS;1. An amide of formula (IV): 1 2 wherein R and R are different and one represents a 5 C 1~ C 6 9 rou P a ud the other represents a C^-C^ alkyl group, with the proviso that, when one of R x and R is propyl, the other is not C^_2 alkyl.
2. A compound as claimed in claim 1 wherein 1 2 either R or R represents isopropyl. 10
3. A process for the prepartion 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 1 2 ester thereof, and R and R are as defined in claim 1
4. A process as claimed in claim 3 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 |
---|---|---|---|
IE2296/81A IE46732B1 (en) | 1978-04-20 | 1978-04-20 | N-(2-(3,4-dialkoxyphenyl)ethyl)-3,4-dialkoxyphenylacetamides |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IE77978A IE46731B1 (en) | 1978-04-20 | 1978-04-20 | Tetra alkoxy substituted 1-benzyl di-and tetra-hydroisoquinolines |
IE2296/81A IE46732B1 (en) | 1978-04-20 | 1978-04-20 | N-(2-(3,4-dialkoxyphenyl)ethyl)-3,4-dialkoxyphenylacetamides |
Publications (2)
Publication Number | Publication Date |
---|---|
IE812296L IE812296L (en) | 1983-04-02 |
IE46732B1 true IE46732B1 (en) | 1983-09-07 |
Family
ID=11018032
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IE77978A IE46731B1 (en) | 1978-04-20 | 1978-04-20 | Tetra alkoxy substituted 1-benzyl di-and tetra-hydroisoquinolines |
IE2296/81A IE46732B1 (en) | 1978-04-20 | 1978-04-20 | N-(2-(3,4-dialkoxyphenyl)ethyl)-3,4-dialkoxyphenylacetamides |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IE77978A IE46731B1 (en) | 1978-04-20 | 1978-04-20 | Tetra alkoxy substituted 1-benzyl di-and tetra-hydroisoquinolines |
Country Status (1)
Country | Link |
---|---|
IE (2) | IE46731B1 (en) |
-
1978
- 1978-04-20 IE IE77978A patent/IE46731B1/en not_active IP Right Cessation
- 1978-04-20 IE IE2296/81A patent/IE46732B1/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
IE780779L (en) | 1979-10-20 |
IE812296L (en) | 1983-04-02 |
IE46731B1 (en) | 1983-09-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7531673B2 (en) | Preparation of amino acid amides | |
US5298657A (en) | Preparation of substituted guanidines | |
HUT64012A (en) | Process for producing benzene derivatives promoting nerve growth factor productiion, as well as pharmaceutical compositions comprising such active ingredient | |
RU1797607C (en) | Process for preparing [@]-@@@-ethyl-2-oxo-1-pyrrolidine acetamide | |
KR0133286B1 (en) | Process for preparing 3-pyrrolidinol | |
KR960008664B1 (en) | Process for the preparation of 2,b-dichlorodiphenylamino acetic acid derivatives | |
IE883744L (en) | Optically active amines and optical resolution using same | |
AU612000B2 (en) | A process for the preparation of pyrrolidone derivatives | |
SU805945A3 (en) | Method of preparing n-substituted lactams | |
US3985756A (en) | Process for producing azasulfonium salts and rearrangement thereof to thio-ethers | |
US4772711A (en) | Method for the preparation of 3-aminoacrylic acid esters | |
IE46732B1 (en) | N-(2-(3,4-dialkoxyphenyl)ethyl)-3,4-dialkoxyphenylacetamides | |
GB1585027A (en) | N-(2-(3,4-dialkoxyphenyl)ethyl)-3,4-dialkoxyphenyl-acetamides | |
US4614830A (en) | Esterification process | |
US4483983A (en) | Substituted derivatives of thiamorpholinone | |
US5290947A (en) | Process for the preparation of pyrrole derivates | |
US4229375A (en) | 1-Aminomethyltricyclo[4.3.1.12,5 ]undecane and acid-addition salts thereof | |
CA1130305A (en) | Process for the preparation of n,n'-disubstituted 2-naphthaleneethanimidamide and intermediates used therein | |
EP0365210A1 (en) | Hydroxamic acid derivatives | |
CA2098663A1 (en) | Process for preparing pyrrolidinylacetamide derivative | |
HU194164B (en) | Process for production of 1,2-dihydroxi-3-//2-indolil-1,1-dialkyl-ethil/-amin/-prophanes | |
US4552967A (en) | Process for the synthesis of intermediates in the preparation of diaminopyridines | |
US4122111A (en) | Carbamoylthiobenzamides and compositions comprising same | |
US4171307A (en) | 5-(4-Bromophenyl)oxazole | |
US3903161A (en) | Ketoamides |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM4A | Patent lapsed |