Claims
- 1. A process for producing a piperidinecarboxylic acid amide derivative represented by formula (9): whereinX represents an alkyl group having 1 to 2 carbon atoms; Y represents a hydrogen atom; and Z represents a CH═CH— group comprising: reacting a 2-oxazoline compound represented by formula (1): wherein X is as defined above, with a piperidine derivative represented by formula (2): wherein Y and Z are as defined above,or a salt thereof, in the presence of an acid.
- 2. The process of claim 1, wherein X is a methyl group.
- 3. The process of claim 1, wherein the acid is selected from the group consisting of boron trifluorode etherate, zinc chloride, p-toluenesulfonic acid, a hydrate thereof and methanesulfonic acid.
- 4. The process of claim 3, wherein the acid is selected from the group consisting of p-toluenesulfonic acid, a hydrate thereof and boron trifluorode etherate.
- 5. The process of claim 4, wherein p-toluenesulfonic acid or a hydrate thereof is used in an amount of 8 to 25 molar % based on the 2-oxazoline compound.
- 6. The process of claim 1, wherein the reaction is conducted in a solvent.
- 7. The process of claim 6, wherein the solvent is selected from the group consisting of halogenated hydrocarbons, aromatic hydrocarbons and hydrocarbons.
- 8. The process of claim 1, wherein the reaction is conducted without any solvent.
- 9. The process of claim 1, wherein the reaction is conducted at a temperature of 50 to 140° C.
- 10. The process of claim 1, wherein X is a methyl group, the acid is selected from the group consisting of p-toluenesulfonic acid, a hydrate thereof and boron trifluorode etherate, and the reaction is conducted at a temperature of 50 to 140° C.
- 11. The process of claim 10, wherein the reaction is conducted in a solvent.
- 12. The process of claim 11, wherein the solvent is selected from the group consisting of halogenated hydrocarbons, aromatic hydrocarbons, and hydrocarbons.
- 13. The process of claim 10, wherein the reaction is conducted without any solvent.
- 14. The process of claim 1, which further comprises isolating the resulting piperidinecarboxylic acid amide derivative.
- 15. The process of claim 1, which further comprises isolating the piperidinecarboxylic acid amide derivative and purifying the piperidinecarboxylic acid amide derivative in the form of free acid or a salt thereof.
Priority Claims (1)
Number |
Date |
Country |
Kind |
9-90564 |
Apr 1997 |
JP |
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Parent Case Info
This application is a Continuation of U.S. application Ser. No. 09/415,066, filed on Oct. 12, 1999, now allowed, which is a Continuation of PCT/JP98/01460, filed Mar. 31, 1998.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
5231105 |
Shoji et al. |
Jul 1993 |
A |
5932593 |
Makino et al. |
Aug 1999 |
A |
Foreign Referenced Citations (4)
Number |
Date |
Country |
0 682 015 |
Nov 1995 |
EP |
3-47168 |
Feb 1991 |
JP |
8-3135 |
Jan 1996 |
JP |
9-176119 |
Jul 1997 |
JP |
Non-Patent Literature Citations (3)
Entry |
Kleine et al., Aminolysis of the Oxazoline Ring of Halomethyl-Substituted Hexahydrooxazolopurines, Arch. Pharm . . . , 303 (4), pp 378-383, 1970 (with Chemical Abstract). |
Iwakura et al., Reaction of Alkylidenepseudoxazolones with Amines, Tetraron Letters, No. 45, pp. 5461-5466, 1966 (with Chemical Abstract). |
Michael J. Fazio, Nucleophilic Ring Opening of 2-Oxazolines with Amines: A Convenient Synthesis for Unsymmetrically Substituted Ethylenediamines, J. Org. Chem., 1984, vol. 49, 4889-4893. |
Continuations (2)
|
Number |
Date |
Country |
Parent |
09/415066 |
Oct 1999 |
US |
Child |
09/750243 |
|
US |
Parent |
PCT/JP98/01460 |
Mar 1998 |
US |
Child |
09/415066 |
|
US |