GB839289A - Acetylenically unsaturated ethanolamines and process for their preparation - Google Patents
Acetylenically unsaturated ethanolamines and process for their preparationInfo
- Publication number
- GB839289A GB839289A GB22841/58A GB2284158A GB839289A GB 839289 A GB839289 A GB 839289A GB 22841/58 A GB22841/58 A GB 22841/58A GB 2284158 A GB2284158 A GB 2284158A GB 839289 A GB839289 A GB 839289A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethanolamine
- benzyl
- phenyl
- butyl
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0839289/IV (b)/1> wherein R1, R2, R4, R5, R6 and R6 are hydrogen, alkyl, aryl, aralkyl or alkaryl, at least one of R1 and R2 being hydrogen; R3 is alkyl, hydroxyalkyl, aryl, aralkyl or alkaryl and R8 is hydrogen, alkyl, alkenyl, aryl, aralkyl, alkaryl or hydroxyalkyl; and acetyl esters thereof; specified products being the N-isobutyl-, benzyl, isopropyl- and hydroxyethyl-N-propynyl - (2) - ethanolamine and N - isopropyl - N - (4 - hydroxy - 4 - methyl - 2 - hexynyl) - ethanolamine. The compounds are prepared by reacting an oxazolidine <FORM:0839289/IV (b)/2> with an acetylene derivative R8CCH, in a solvent, at a temperature of 0-30 DEG C., in the presence of cuprous ions and at a pressure between atmospheric and 14 inches of mercury above atmospheric. The products may subsequently be etherified or converted to esters, for example acetyl esters. Oxazolidines of the formula II used as starting materials, e.g. 3-isobutyl-, 3-t-butyl-, 2-n-butyl-3-t-butyl-, 3-t-butyl-5-phenyl-, 3-benzyl-, 2-phenyl-3-benzyl-, 2-n-propyl-3-benzyl-, 3-isopropyl-, 3-b -hydroxyethyl-, 2-phenyl-3-methyl-, 3-phenyl-, 3-t-octyl- and 2-n-propyl-3-t-octyl-, oxazolidine are made by the action of an aldehyde R1R2C:O on an ethanolamine of the formula R3NH.CR4R5.CR6R7.OH (III). Ethanolamines of the formula III are made by reacting an amine with a 1:2-epoxide or by reductive alkylation of an ethanolamine with an aldehyde or ketone and catalytic hydrogenation.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US839289XA | 1957-07-18 | 1957-07-18 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB839289A true GB839289A (en) | 1960-06-29 |
Family
ID=22181573
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB22841/58A Expired GB839289A (en) | 1957-07-18 | 1958-07-16 | Acetylenically unsaturated ethanolamines and process for their preparation |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB839289A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0837050A1 (en) * | 1996-10-15 | 1998-04-22 | Basf Aktiengesellschaft | Process for the preparation of N-hydroxyalkyl substituted aminoalkynes through heterogenous catalysis |
WO2010091142A1 (en) * | 2009-02-04 | 2010-08-12 | President And Fellows Of Harvard College | Compositions and methods for labeling and imaging phospholipids |
-
1958
- 1958-07-16 GB GB22841/58A patent/GB839289A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0837050A1 (en) * | 1996-10-15 | 1998-04-22 | Basf Aktiengesellschaft | Process for the preparation of N-hydroxyalkyl substituted aminoalkynes through heterogenous catalysis |
WO2010091142A1 (en) * | 2009-02-04 | 2010-08-12 | President And Fellows Of Harvard College | Compositions and methods for labeling and imaging phospholipids |
US8987514B2 (en) | 2009-02-04 | 2015-03-24 | President And Fellows Of Harvard College | Compositions and methods for labeling and imaging phospholipids |
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