CA2461574A1 - Process for preparing vanillylamine hyrochloride - Google Patents
Process for preparing vanillylamine hyrochloride Download PDFInfo
- Publication number
- CA2461574A1 CA2461574A1 CA002461574A CA2461574A CA2461574A1 CA 2461574 A1 CA2461574 A1 CA 2461574A1 CA 002461574 A CA002461574 A CA 002461574A CA 2461574 A CA2461574 A CA 2461574A CA 2461574 A1 CA2461574 A1 CA 2461574A1
- Authority
- CA
- Canada
- Prior art keywords
- process according
- vanillylamine
- salts
- preparing
- acid
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/58—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Process for preparing vanillylamine or one of the salts thereof by a) reacting vanillin with hydroxylamine or the salts thereof in the presence of an organic salt, which may optionally be produced in situ, and b) subsequently hydrogenating the resulting vanillyloxime with hydrogen in the presence of a suitable catalyst and an organic and/or inorganic acid, characterised in that step a) is carried out in an inorganic or organic acid as diluent.
Claims (11)
1) Process for preparing vanillylamine or one of the salts thereof by a) reacting vanillin with hydroxylamine or the salts thereof in the presence of an organic salt, which may optionally be produced in situ, and b) subsequently hydrogenating the resulting vanillyloxime with hydrogen in the presence of a suitable catalyst and an organic and/or inorganic acid, characterised in that step a) is carried out in an inorganic or organic acid as diluent.
2) Process according to claim 1, characterised in that steps a) and b) are carried out in a one-pot process.
3) Process according to claim 1 or 2, characterised in that in step a) sodium acetate and glacial acetic acid are used.
4) Process according to one of claims 1 to 3, characterised in that in step a) vanillin is reacted with hydroxylamine hydrochloride.
5) Process according to one of claims 1 to 4, characterised in that in step b) Pd/C or Pt/C is used as catalyst.
6) Process according to one of claims 1 to 5, characterised in that the hydrogenation step b) is carried out in the presence of glacial acetic acid and concentrated hydrochloric acid.
7) Process according to one of claims 1 to 6, characterised in that the reaction temperature in step a) is 15 °C to 50 °C.
8) Process according to one of claims 1 to 6, characterised in that the reaction temperature in step b) is 0°C to 70° C.
9) Process according to one of claims 1 to 8, characterised in that vanillin is used in a molar ratio to hydroxylamine or a salt thereof of 1:2 to 2:1.
10) Use of the vanillylamine or one of the salts thereof obtained by a process according to one of claims 1 to 9 for preparing pharmaceutically effective compounds.
11) Use of the vanillylamine or one of the salts thereof obtained by a process according to one of claims 1 to 9 for preparing pelargonic acid vanillylamide.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10147958A DE10147958A1 (en) | 2001-09-28 | 2001-09-28 | Process for the preparation of yanillylamine hydrochloride |
| DE10147958.1 | 2001-09-28 | ||
| PCT/EP2002/010803 WO2003029208A2 (en) | 2001-09-28 | 2002-09-26 | Method for producing vanillylamine hydrochloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2461574A1 true CA2461574A1 (en) | 2003-04-10 |
| CA2461574C CA2461574C (en) | 2011-01-11 |
Family
ID=7700689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2461574A Expired - Fee Related CA2461574C (en) | 2001-09-28 | 2002-09-26 | Process for preparing vanillylamine hyrochloride |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1432675B1 (en) |
| JP (1) | JP4272521B2 (en) |
| AT (1) | ATE312071T1 (en) |
| AU (1) | AU2002333879A1 (en) |
| CA (1) | CA2461574C (en) |
| DE (2) | DE10147958A1 (en) |
| ES (1) | ES2253581T3 (en) |
| WO (1) | WO2003029208A2 (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE760746C (en) * | 1941-02-21 | 1953-05-18 | Boehringer & Soehne Gmbh | Process for the preparation of primary amines |
| FR2397387A1 (en) * | 1976-04-27 | 1979-02-09 | Serobiologiques Lab Sa | 4,4'-BIS-FORMYL-POLYHALO-DIPHENOXYALCANES, PROCESS FOR PREPARATION AND APPLICATION TO THE SYNTHESIS OF 4,4'-DICYANO-POLYHALO-DIPHENOXYALCANES |
-
2001
- 2001-09-28 DE DE10147958A patent/DE10147958A1/en not_active Ceased
-
2002
- 2002-09-26 AU AU2002333879A patent/AU2002333879A1/en not_active Abandoned
- 2002-09-26 JP JP2003532458A patent/JP4272521B2/en not_active Expired - Lifetime
- 2002-09-26 ES ES02800124T patent/ES2253581T3/en not_active Expired - Lifetime
- 2002-09-26 DE DE50205226T patent/DE50205226D1/en not_active Expired - Lifetime
- 2002-09-26 AT AT02800124T patent/ATE312071T1/en active
- 2002-09-26 EP EP02800124A patent/EP1432675B1/en not_active Expired - Lifetime
- 2002-09-26 WO PCT/EP2002/010803 patent/WO2003029208A2/en active IP Right Grant
- 2002-09-26 CA CA2461574A patent/CA2461574C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005527478A (en) | 2005-09-15 |
| ATE312071T1 (en) | 2005-12-15 |
| ES2253581T3 (en) | 2006-06-01 |
| EP1432675A2 (en) | 2004-06-30 |
| AU2002333879A1 (en) | 2003-04-14 |
| EP1432675B1 (en) | 2005-12-07 |
| DE10147958A1 (en) | 2003-04-30 |
| DE50205226D1 (en) | 2006-01-12 |
| WO2003029208A2 (en) | 2003-04-10 |
| CA2461574C (en) | 2011-01-11 |
| JP4272521B2 (en) | 2009-06-03 |
| WO2003029208A3 (en) | 2003-09-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20130926 |