GB716649A - Preparation of tertiary alicyclic amines - Google Patents

Preparation of tertiary alicyclic amines

Info

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
Application number
GB9384/52A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Monsanto Chemicals Ltd
Monsanto Chemical Co
Original Assignee
Monsanto Chemicals Ltd
Monsanto Chemical Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Monsanto Chemicals Ltd, Monsanto Chemical Co filed Critical Monsanto Chemicals Ltd
Publication of GB716649A publication Critical patent/GB716649A/en
Expired legal-status Critical Current

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.
GB9384/52A 1951-04-17 1952-04-15 Preparation of tertiary alicyclic amines Expired GB716649A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (1)

* Cited by examiner, † Cited by third party
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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