GB800670A - Method of producing n-alkyl-piperidine ª‡-carboxylic acid amides and n-alkyl-pyrrolidine ª‡-carboxylic acid amides - Google Patents
Method of producing n-alkyl-piperidine ª‡-carboxylic acid amides and n-alkyl-pyrrolidine ª‡-carboxylic acid amidesInfo
- Publication number
- GB800670A GB800670A GB433/57A GB43357A GB800670A GB 800670 A GB800670 A GB 800670A GB 433/57 A GB433/57 A GB 433/57A GB 43357 A GB43357 A GB 43357A GB 800670 A GB800670 A GB 800670A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- carboxylic acid
- alkyl
- give
- malonic
- 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
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 3
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 abstract 1
- MRXFZJUGNOQIEF-UHFFFAOYSA-N 2-(2-cyanoethyl)propanedioic acid Chemical compound OC(=O)C(C(O)=O)CCC#N MRXFZJUGNOQIEF-UHFFFAOYSA-N 0.000 abstract 1
- UXCHQJIKLPXKRI-UHFFFAOYSA-N 2-(3-cyanopropyl)propanedioic acid Chemical compound OC(=O)C(C(O)=O)CCCC#N UXCHQJIKLPXKRI-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- JWFVGQJHBVZECV-UHFFFAOYSA-N 5-amino-2-chloropentanoic acid hydrochloride Chemical compound Cl.ClC(C(=O)O)CCCN JWFVGQJHBVZECV-UHFFFAOYSA-N 0.000 abstract 1
- CBRSWZYPLFGNGQ-UHFFFAOYSA-N 6-amino-2-chlorohexanoic acid;hydrochloride Chemical compound Cl.NCCCCC(Cl)C(O)=O CBRSWZYPLFGNGQ-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- -1 aryl amide Chemical class 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- YJJLOESDBPRZIP-UHFFFAOYSA-N diethyl 2-(2-cyanoethyl)propanedioate Chemical compound CCOC(=O)C(CCC#N)C(=O)OCC YJJLOESDBPRZIP-UHFFFAOYSA-N 0.000 abstract 1
- TXBCSTVTPWJWRR-UHFFFAOYSA-N diethyl 2-(3-cyanopropyl)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)CCCC#N TXBCSTVTPWJWRR-UHFFFAOYSA-N 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
N - Alkyl - piperidine or pyrrolidine - a - carboxylic acids of the formula <FORM:0800670/IV (b)/1> and <FORM:0800670/IV (b)/2> wherein R is an alkyl group and Ar is a 2-alkyl benzene of 2:6-dialkyl benzene group, are made by reducing a 3-cyano-propyl malonic diethyl ester or 2-cyano-ethyl malonic diethyl ester, for example by hydrogenation in the presence of Raney nickel to give 2-keto-hexamethyleneimine-3-carboxylic acid ethyl ester or 2-piperidone-3-carboxylic acid ethyl ester, chlorinating, suitably with sulphuryl chloride, and boiling with hydrochloric acid to give 2-chloro-6-amino-caproic acid hydrochloride or 2-chloro-5-amino-valeric acid hydrochloride, converting to the acid chloride, treating with an aromatic amine ArNH2 to give the hydrochloride of the corresponding a -chloro-o -amino-caproic or valeric aryl amide, treating with alkali to effect ring closure to the piperidine or pyrrolidine-a -carboxylic acid arylamide and alkylating the nuclear nitrogen atom to give the desired product. Examples describe the preparation of N-ethyl pipecolyl-2:6-xylidide and N-methyl-prolyl-2:6-xylidide. Starting materials. The diethyl esters of 3-cyanopropyl malonic acid and 2-cyanoethyl malonic acid are made by reacting diethyl malonate with g -bromo butyronitrile or acrylonitrile. Specification 770,129 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE800670X | 1956-01-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB800670A true GB800670A (en) | 1958-08-27 |
Family
ID=20341810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB433/57A Expired GB800670A (en) | 1956-01-23 | 1957-01-04 | Method of producing n-alkyl-piperidine ª‡-carboxylic acid amides and n-alkyl-pyrrolidine ª‡-carboxylic acid amides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB800670A (en) |
-
1957
- 1957-01-04 GB GB433/57A patent/GB800670A/en not_active Expired
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