GB716649A - Preparation of tertiary alicyclic amines - Google Patents
Preparation of tertiary alicyclic aminesInfo
- Publication number
- GB716649A GB716649A GB9384/52A GB938452A GB716649A GB 716649 A GB716649 A GB 716649A GB 9384/52 A GB9384/52 A GB 9384/52A GB 938452 A GB938452 A GB 938452A GB 716649 A GB716649 A GB 716649A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formaldehyde
- formic acid
- cyclohexyl
- methyl
- mol
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/35—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing only non-condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Tertiary amines having the general formula R1-N(CH3)-R2 in which R1 is a cycloalkyl group and R2 is an alkyl or cycloalkyl group are prepared by treating a primary or secondary amine having the general formula R1-NH-R3, in which R1 is as above defined and R3 is hydrogen or an alkyl or cycloalkyl group, with formic acid and formaldehyde and heating until evolution of carbon dioxide commences, the proportions of formic acid and formaldehyde being at least substantially sufficient to introduce one methyl group into a secondary amine R1NHR2 or two methyl groups into a primary amine R1NH2, R1 and R2 being as defined above. Preferably, more than 1 mol. of formic acid and substantially 1 mol. of formaldehyde are used per methyl group to be introduced. In an example, cyclohexylamine (1 mol.) is gradually added to about 2.2 mols. formic acid cooled to 5 DEG C., followed by addition of about 2.2 mols. formaldehyde, whereupon the mixture is heated to 50 DEG C. and after evolution of carbon dioxide to 90-95 DEG C.; on working up N : N-dimethyl cyclohexylamine is obtained as substantially the sole product, a small amount of N-mono cyclohexylamine being obtained if the heating after evolution of carbon dioxide is omitted. Other starting materials mentioned are those amines R1-NH-R3 wherein R1 may be cyclohexyl, methyl cyclohexyl, dimethyl cyclohexyl and ethyl cyclohexyl and R3 is hydrogen or methyl, ethyl or propyl.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US716649XA | 1951-04-17 | 1951-04-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB716649A true GB716649A (en) | 1954-10-13 |
Family
ID=22102789
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB9384/52A Expired GB716649A (en) | 1951-04-17 | 1952-04-15 | Preparation of tertiary alicyclic amines |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB716649A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4996316A (en) * | 1987-12-09 | 1991-02-26 | Hoechst Aktiengesellschaft | Process for the preparation of tertiary N, N-dimethylamines |
-
1952
- 1952-04-15 GB GB9384/52A patent/GB716649A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4996316A (en) * | 1987-12-09 | 1991-02-26 | Hoechst Aktiengesellschaft | Process for the preparation of tertiary N, N-dimethylamines |
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