IE891100L - A process for the preparation of an n-acetyl-6-aminohexanoic¹acid derivative - Google Patents
A process for the preparation of an n-acetyl-6-aminohexanoic¹acid derivativeInfo
- Publication number
- IE891100L IE891100L IE891100A IE110089A IE891100L IE 891100 L IE891100 L IE 891100L IE 891100 A IE891100 A IE 891100A IE 110089 A IE110089 A IE 110089A IE 891100 L IE891100 L IE 891100L
- Authority
- IE
- Ireland
- Prior art keywords
- acetyl
- preparation
- aminohexanoic acid
- solvent
- acid derivative
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000002904 solvent Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 4
- 239000002798 polar solvent Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 150000003751 zinc Chemical class 0.000 claims description 4
- WDSCBUNMANHPFH-UHFFFAOYSA-N acexamic acid Chemical class CC(=O)NCCCCCC(O)=O WDSCBUNMANHPFH-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 239000011787 zinc oxide Substances 0.000 description 3
- 229960002684 aminocaproic acid Drugs 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
Description
61 51 7
2
The present invention relates to a process for the preparation of an W-acetyl-5-aminohexanoic acid derivatives particularly the zinc salt of said acid.
This saltp of formula:
£CH3-C0NH-(CH2)5 - C0072Zn has antiulcer properties.
The process of the present invention is characterised in that zinc oxide, cheaper to obtain than other derivatives, is reacted with M-acetyl-6-aminohexanoic acid in a polar solvent or mixture of such solvents, preferably water.
The temperature used may reach the boiling point of the solvent; preferably a temperature of about 80°C is used„
The salt may be isolated by crystallisation from the same solvent of a further solvent in which it is less soluble may be added to increase the yield, followed by filtration and drying.
To facilitate the explanation, the invention is illustrated by the following examples, while not being limited thereto™
EXAMPLE 1
2.0 g of N-acetyl-6-aminohexanoic acid were dissolved in 6 ml of distilled water. The temperature of the solution was raised to 80°C and 0.47 g of zinc oxide were added gradually. Once the addition had ended, the reaction
mixture was stirred at the above temperature for 15 minutes, after which it was allowed to cool. When the temperature had dropped to between 40 and 50°C 8 & ml of acetone were added and the mixture was cooled to -5°C„ It was allowed to rest at that temperature for 12 hours,, was filtered, washed in acetone and dried at 60°C.
A white crystalline powder which is the zinc salt of N-acetyl-=6-aminohexanoic acid was thus obtained.
Melting point: 193-196°C.
Elementary analysis:
Calculated (%) for C^gHjjgNgOgZn C: 46.94; H: 6.84; N: 6.84; 0: 23.41; and Zn: 15.96
Found (%):
C: 46.90; H: 6.67; N: 6.79; and Zn: 15.88 EXAMPLE 2
2.0 g of N-acetyl-6-aminohexanoic acid and 0.47 g of zinc oxide were poured into a reactor of appropriate capacity and 6 ml of distilled water were added. The temperature was raised, under stirrings, to 90°C and held for 30 minutes. The mixture was allowed to cooled to room temperature and thereafter was cooled to 02C. It was allowed to rest for 12 hours at 0°C, was filtered, washed with acetone and dried at 60°C.
A white crystalline compound having the same characteristics as that of Example 1 was thus obtained.
Claims (6)
1.- A process for the preparation of an N-acety1-6-aminohexanoic acid derivative, namely the zinc salt thereof of formula £CHg-C0WH-(CH2)5 - COQ722'n!> characterised in that N-acetyl-6-araxnohexanoic acid is reacted with sine oxide in a polar solvent or a mixture of polar solvents,
2.- The process of claim 1, characterised in that said polar solvent is water.
3»- The process of claim 1, characterised in that the reaction temperature is equal to or less than the boiling point of the solvent.
4»- The process of claim 1, characterised in that said zinc salt is isolated bv crystallisation from the same solvent, followed by filtration and drying™
5„- A process according to claim 1 for the preparation of an N-acetyl-6-aminohexanoic acid derivative of the formula given therein, substantially as hereinbefore described and exemplified,
6.- An M-acetyl-6-aminohexanoic acid derivative of the formula given in claim 1, whenever prepared by a process claimed in a preceding claim. Dated this the 6th day of April, 1989 F. R. KELil &fcjp4/| BY EXECUTIVE 27 Clyde Road, Ballsbridge, Dublin 4 AGENTS FOR THE APPLICANTS
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES8801281A ES2009266A6 (en) | 1988-04-27 | 1988-04-27 | Preparation of the zinc salt of N-acetyl-6-aminohexanoic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE891100L true IE891100L (en) | 1989-10-27 |
| IE61517B1 IE61517B1 (en) | 1994-11-16 |
Family
ID=8256036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE110089A IE61517B1 (en) | 1988-04-27 | 1989-04-06 | A process for the preparation of an N-acetyl-6-aminohexano acid derivative |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JP2588018B2 (en) |
| BE (1) | BE1002546A3 (en) |
| DE (1) | DE3913627C2 (en) |
| DK (1) | DK201589A (en) |
| ES (1) | ES2009266A6 (en) |
| FR (1) | FR2630737B1 (en) |
| GB (1) | GB2218090B (en) |
| IE (1) | IE61517B1 (en) |
| IT (1) | IT1229653B (en) |
| NL (1) | NL8900901A (en) |
| PT (1) | PT90372B (en) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1311466A (en) * | 1968-12-23 | 1973-03-28 | Herbert Ltd A | Vertical spindle lathe for use in a machining complex |
| FR2062873B1 (en) * | 1969-09-25 | 1973-07-13 | Choay Sa | |
| FR2147822B1 (en) * | 1971-07-30 | 1974-10-18 | Centre Etd Ind Pharma | |
| ES466455A1 (en) * | 1978-01-30 | 1978-10-16 | Vinas Lab | Procedure for the preparation of a new caprolactama derivative. (Machine-translation by Google Translate, not legally binding) |
-
1988
- 1988-04-27 ES ES8801281A patent/ES2009266A6/en not_active Expired
-
1989
- 1989-04-06 IE IE110089A patent/IE61517B1/en not_active IP Right Cessation
- 1989-04-11 GB GB8908095A patent/GB2218090B/en not_active Expired - Fee Related
- 1989-04-11 NL NL8900901A patent/NL8900901A/en active Search and Examination
- 1989-04-17 JP JP1098613A patent/JP2588018B2/en not_active Expired - Fee Related
- 1989-04-21 IT IT8920252A patent/IT1229653B/en active
- 1989-04-25 FR FR898905461A patent/FR2630737B1/en not_active Expired - Fee Related
- 1989-04-25 DE DE3913627A patent/DE3913627C2/en not_active Expired - Fee Related
- 1989-04-26 DK DK201589A patent/DK201589A/en not_active Application Discontinuation
- 1989-04-26 PT PT90372A patent/PT90372B/en active IP Right Grant
- 1989-04-26 BE BE8900464A patent/BE1002546A3/en active
Also Published As
| Publication number | Publication date |
|---|---|
| DK201589D0 (en) | 1989-04-26 |
| DE3913627A1 (en) | 1989-11-16 |
| IE61517B1 (en) | 1994-11-16 |
| PT90372B (en) | 1995-03-31 |
| GB2218090A (en) | 1989-11-08 |
| IT1229653B (en) | 1991-09-06 |
| DE3913627C2 (en) | 1997-12-11 |
| JPH02180859A (en) | 1990-07-13 |
| NL8900901A (en) | 1989-11-16 |
| JP2588018B2 (en) | 1997-03-05 |
| DK201589A (en) | 1989-10-28 |
| GB2218090B (en) | 1991-12-11 |
| ES2009266A6 (en) | 1989-09-16 |
| FR2630737B1 (en) | 1991-11-08 |
| GB8908095D0 (en) | 1989-05-24 |
| IT8920252A0 (en) | 1989-04-21 |
| BE1002546A3 (en) | 1991-03-19 |
| PT90372A (en) | 1989-11-10 |
| FR2630737A1 (en) | 1989-11-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |