GB609488A - Production of propyldiamines and acridine compounds of propyldiamines - Google Patents
Production of propyldiamines and acridine compounds of propyldiaminesInfo
- Publication number
- GB609488A GB609488A GB20031/45A GB2003145A GB609488A GB 609488 A GB609488 A GB 609488A GB 20031/45 A GB20031/45 A GB 20031/45A GB 2003145 A GB2003145 A GB 2003145A GB 609488 A GB609488 A GB 609488A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- prepared
- propylamino
- general formula
- isobutylamino
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
- C07D219/10—Nitrogen atoms attached in position 9
- C07D219/12—Amino-alkylamino radicals attached in position 9
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
Abstract
Acridines of the general formula <FORM:0609488/IV(b)/1> , wherein R in both instances represents the same saturated non-tertiary hydrocarbon radical having from three to seven carbon atoms, are prepared by condensing in phenol 2-methoxy-6:9-dichloroacridine and a diamine of the general formula <FORM:0609488/IV(b)/2> , where R has the significance indicated above. The bases may be converted to their salts by the addition of acids. In examples (1) to (5), 9-[11-methyl-31-(di-n-butylamino)-propylamino]-, 9-[11-methyl-31-(di-isopropylamino)-propylamino]-, 9-[11-methyl-31-(di-isoamylamino) - propylamino]-, 9 - [11 - methyl - 31 - (di - cyclohexylamino) - propylamino]- and 9 - [11 - methyl-31-(di-isobutylamino) -propylamino]-2-methoxy-6-chloroacridines are prepared by condensing 2 - methoxy - 6 : 9 - dichloroacridine with 3 - (di - n - butylamino)-, 3 - (di - isopropylamino)-, 3 - (di - isoamylamino)-, 3 - (di - cyclohexylamino)-, and 3 - (di - isobutylamino) - 1 - methyl-propylamines, and are converted in their corresponding dihydrochlorides; (7) the substituted acridines prepared in (1) to (5) are converted into their corresponding dihydrobromides, sulphates, nitrates, phosphates, lactates and propionates. 1 - Disubstituted - amino - 3 - butanones of the general formula <FORM:0609488/IV(b)/3> are prepared by treating the hydrochloride of an amine of the general formula <FORM:0609488/IV(b)/4> with acetone, formaldehyde and water, where R has the significance already indicated. In examples (1) to (5), 1-di-n-butylamino-, 1-di-isopropylamino-, 1-di-isoamylamino-, 1-di-cyclohexylamino- and 1-di-isobutylamino-3-butanones are prepared. 1 - Disubstituted - amino - 3 - butanoneoximes of the general formula <FORM:0609488/IV(b)/5> , where R has the significance already indicated, are prepared by reacting 1-disubstituted-amino-3-butanones, of the general formula given above, with hydroxylamine hydrochloride. In examples (1) to (5), 1-di-n-butylamino-, 1-di-isopropylamino-, 1 - di - isoamylamino-, 1 - di - cyclohexylamino- and 1 - di - isobutylamino - 3 - butanoneoximes are prepared. 1 - Methyl - 3 - (disubstituted amino) propylamines of the general formula <FORM:0609488/IV(b)/6> , where R has the significance already indicated, are prepared by reducing the above 1-disubstituted-amino-3-butanoneoximes, e.g. by treating an alcohol solution containing the oxime with hydrogen under pressure and heat or with metallic sodium. In examples (1) to (5), 3-(di-n-butylamino)-, 3-(di-isopropylamino)-, 3-(di-isoamylamino)-3-(di-cyclohexylamino)-, and 3 - (di - isobutylamino) - 1 - methyl - propylamines are obtained by reducing the corresponding oximes given above with metallic sodium in the presence of absolute alcohol.ALSO:Acridines of the general formula <FORM:0609488/IV (c)/1> wherein R in both instances represents the same saturated non-tertiary hydrocarbon radical having from three to seven carbon atoms, are prepared by condensing in phenol 2-methoxy-6 : 9-dichloroacridine and a diamine of the general formula <FORM:0609488/IV (c)/2> where R has the significance indicated above. The bases may be converted to their salts by the addition of acids. In examples (1) to (5), 9 - [11 - methyl - 31 - (di - n - butylamino) - propylamino]-, 9-[11-methyl-31-(di-isopropylamino) - propylamino]-, 9 - [11 - methyl - 31 - (di - isoamyl amino) - propylamino]-, 9 - [11 - methyl - 31 - (di - cyclohexylamino) - propylamino] - and 9 - [11 - methyl-31-(di-isobutylamino)-propylamino]-2-methoxy - 6 - chloroacridines are prepared by condensing 2 - methoxy - 6 : 9 - dichloroacridine with 3 - (di - n - butylamino)-, 3 - (di - isopropylamino)-, 3 - (di - isoamylamino)-, 3 - (di - cyclohexylamino)-, and 3 - (di - isobutylamino) - 1 - methyl-propylamines, and converted in their corresponding dihydrochlorides; (7) the substituted acridines prepared in (1) to (5) are converted into their corresponding dihydrobromides, sulphates, nitrates, phosphates, lactates and propionates.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US609488XA | 1944-08-07 | 1944-08-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB609488A true GB609488A (en) | 1948-10-01 |
Family
ID=22032738
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB20031/45A Expired GB609488A (en) | 1944-08-07 | 1945-08-03 | Production of propyldiamines and acridine compounds of propyldiamines |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB609488A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003514888A (en) * | 1999-11-25 | 2003-04-22 | ビーエーエスエフ アクチェンゲゼルシャフト | Method for producing optically active amine |
-
1945
- 1945-08-03 GB GB20031/45A patent/GB609488A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003514888A (en) * | 1999-11-25 | 2003-04-22 | ビーエーエスエフ アクチェンゲゼルシャフト | Method for producing optically active amine |
JP4776846B2 (en) * | 1999-11-25 | 2011-09-21 | ビーエーエスエフ ソシエタス・ヨーロピア | Method for producing optically active amine |
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