GB598312A - Improvements in or relating to the preparation of aryl aliphatic diamines - Google Patents
Improvements in or relating to the preparation of aryl aliphatic diaminesInfo
- Publication number
- GB598312A GB598312A GB7882/45A GB788245A GB598312A GB 598312 A GB598312 A GB 598312A GB 7882/45 A GB7882/45 A GB 7882/45A GB 788245 A GB788245 A GB 788245A GB 598312 A GB598312 A GB 598312A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- isopropylbenzylamino
- schiff
- general formula
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Aryl aliphatic diamines having therapeutic activity and of the general formula <FORM:0598312/IV/1> in which R1 represents an alkyl group, R2 an alkylene group and R3 and R4 hydrogen atoms or alkyl groups or groups of the formula <FORM:0598312/IV/2> are obtained by the reaction of an aldehyde of the formula <FORM:0598312/IV/3> with a compound of the formula <FORM:0598312/IV/4> and reduction of the Schiff's base obtained. It is also possible when preparing N-substituted derivatives to carry out the process in two stages, i.e. to prepare first the compound in which R3 and R4 are hydrogen atoms and subsequently to react this with the same or a different aldehyde followed by reduction of the resulting Schiff's base. The products may also be obtained by condensing a compound of the formula <FORM:0598312/IV/5> (where X is a halogen atom) with a compound of the general formula <FORM:0598312/IV/6> In examples: (1) cuminic aldehyde is condensed with ethylene diamine monohydrate and reduced with sodium in alcohol to give 1-(p-isopropylbenzylamino)-2-aminoethane which is purified as its hydrochloride; (2) cuminyl chloride is heated in a sealed tube with ethylene diamine monohydrate in alcohol giving the product of (1); (3) cuminyl chloride is heated in a sealed tube with 1-diethylamino-4-aminopentane giving 1-diethylamino-4-(p-isopropylbenzylamino) - pentane; (4) 1 - (p - isopropyl - benzylamino)-2-aminoethane prepared according to (1) or (2) is treated with diethyl acetaldehyde and the resultant Schiff's base is reduced with sodium in amyl alcohol to give 1-(p-isopropylbenzylamino) - 2 - (21 - ethylbutylamino) - ethane. The Specification as open to inspection under Sect. 91 comprises also the preparation of other amines of the general formula <FORM:0598312/IV/7> where R is an alkyl group or a halogen atom, R1 is hydrogen or an alkyl or aralkyl group and R2, R3 and R4 as above defined, by any known methods, including additionally the reaction of an amine of the type R.C6H4.NHR1 with a halogenated aliphatic amine. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR598312X | 1941-12-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB598312A true GB598312A (en) | 1948-02-16 |
Family
ID=8968815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7882/45A Expired GB598312A (en) | 1941-12-10 | 1945-03-28 | Improvements in or relating to the preparation of aryl aliphatic diamines |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB598312A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2582292A (en) * | 1949-02-03 | 1952-01-15 | White Lab Inc | Preparation of benzal-imino compounds |
| US2619502A (en) * | 1950-06-23 | 1952-11-25 | Gen Aniline & Film Corp | N,n''-dibenzyl-n,n',n''-trialkyl-dialkylene triamines |
| US2772312A (en) * | 1953-12-31 | 1956-11-27 | Distillers Co Yeast Ltd | Preparation of n:n'-dibenzyl ethylene diamine |
| CN107922585A (en) * | 2015-09-01 | 2018-04-17 | Sika技术股份公司 | Low emission composition epoxy resin |
-
1945
- 1945-03-28 GB GB7882/45A patent/GB598312A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2582292A (en) * | 1949-02-03 | 1952-01-15 | White Lab Inc | Preparation of benzal-imino compounds |
| US2619502A (en) * | 1950-06-23 | 1952-11-25 | Gen Aniline & Film Corp | N,n''-dibenzyl-n,n',n''-trialkyl-dialkylene triamines |
| US2772312A (en) * | 1953-12-31 | 1956-11-27 | Distillers Co Yeast Ltd | Preparation of n:n'-dibenzyl ethylene diamine |
| CN107922585A (en) * | 2015-09-01 | 2018-04-17 | Sika技术股份公司 | Low emission composition epoxy resin |
| AU2016315246B2 (en) * | 2015-09-01 | 2021-02-18 | Sika Technology Ag | Low-emission epoxy resin composition |
| CN113321586A (en) * | 2015-09-01 | 2021-08-31 | Sika技术股份公司 | Low emission epoxy resin composition |
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