GB801169A - Process for the preparation of 2 (alpha-aminoethyl)-furan and derivatives thereof - Google Patents
Process for the preparation of 2 (alpha-aminoethyl)-furan and derivatives thereofInfo
- Publication number
- GB801169A GB801169A GB19836/57A GB1983657A GB801169A GB 801169 A GB801169 A GB 801169A GB 19836/57 A GB19836/57 A GB 19836/57A GB 1983657 A GB1983657 A GB 1983657A GB 801169 A GB801169 A GB 801169A
- Authority
- GB
- United Kingdom
- Prior art keywords
- furan
- aminoethyl
- hydrogen
- prepared
- ammonia
- 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
2-(a -aminoethyl)-furan is prepared by reacting 2-acetylfuran with ammonium hydroxide and hydrogen in an aqueous (including aqueous/alcoholic) system in the presence of an hydrogenation catalyst, preferably an activated form of nickel, such as sponge nickel or Raney nickel, although any catalyst which will promote selective reductive amination of the carbonyl group, without leading to reduction of the furan ring may be used. The 2-(a -aminoethyl)-furan may be recovered as such or converted in situ to a salt, e.g. hydrochloride or a 2-(a -acylamidoethyl)-furan, e.g. 2-(a -acetamidoethyl)-furan. The ammonia may be introduced as liquid ammonia, but preferably as ammonium hydroxide, which under optimum conditions represents an ammonia concentration of ca. 10-30 per cent by weight of the water present in the system. The ratio of ammonia to ketone may be as low as 1 : 1, but is preferably at least 4 : 1. The hydrogen is also preferably present in excess. The reaction may be conducted at room temperature, but preferably at about 50-75 DEG C., optionally about 60-65 DEG C. and at an hydrogen pressure as low as about 1 atmos., but preferably about 20-60 p.s.i.g. It is preferred to include a solvent, miscible with both 2-acetylfuran and the product, e.g. a lower alkanol such as isopropanol. In examples: (1) 2-(a -aminoethyl)-furan is prepared by reacting 2-acetylfuran, ammonium hydroxide and hydrogen, in the presence of a Raney nickel catalyst and isopropanol; (2) 2-(a -aminoethyl)-furan is prepared similarly and converted to the acetate by means of glacial acetic acid; (3) this acetate is acetylated with acetic anhydride in pyridine solution to give 2-(a -acetamidoethyl)-furan; (4) 2-(a -aminoethyl)-furan together with some, presumably, N,N - bis - (a - furylethyl) - amine is prepared as in (1), but using a sponge nickel catalyst; (5) the crude 2-(a -aminoethyl)-furan from (4) is converted to the hydrochloride with HCl; the sulphate and phosphate are also mentioned.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US801169XA | 1956-06-25 | 1956-06-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB801169A true GB801169A (en) | 1958-09-10 |
Family
ID=22155364
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB19836/57A Expired GB801169A (en) | 1956-06-25 | 1957-06-24 | Process for the preparation of 2 (alpha-aminoethyl)-furan and derivatives thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB801169A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014209595A1 (en) * | 2013-06-28 | 2014-12-31 | Archer Daniels Midland Company | Tetrahydrofuran-2,5-dicarbaldehydes (diformyl-tetrahydrofuran, dfthf) and process for making the same |
CN109824629A (en) * | 2019-02-27 | 2019-05-31 | 南京工业大学 | method for preparing 3-amino-5- (α -aminoethyl) tetrahydrofuran by using N-acetyl-D-glucose |
-
1957
- 1957-06-24 GB GB19836/57A patent/GB801169A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014209595A1 (en) * | 2013-06-28 | 2014-12-31 | Archer Daniels Midland Company | Tetrahydrofuran-2,5-dicarbaldehydes (diformyl-tetrahydrofuran, dfthf) and process for making the same |
CN109824629A (en) * | 2019-02-27 | 2019-05-31 | 南京工业大学 | method for preparing 3-amino-5- (α -aminoethyl) tetrahydrofuran by using N-acetyl-D-glucose |
CN109824629B (en) * | 2019-02-27 | 2022-12-09 | 南京工业大学 | Method for preparing 3-amino-5- (alpha-aminoethyl) tetrahydrofuran by using N-acetylglucosamine |
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