US 11,299,451 B2Granted

Method for synthesizing 2-(1-cyclohexenyl)ethylamine

AssigneeFudan University

InventorsFener Chen, Dang Cheng, Zedu Huang, Zhining Li, Meifen Jiang, Yuan Tao

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Abstract

A method for synthesizing 2-(1-cyclohexenyl)ethylamine. Cyclohexanone (II) is reacted with a Grignard reagent in a first organic solvent to produce 1-vinylcyclohexanol (III), which is then subjected to chlorination and rearrangement reaction with a chlorinating reagent in a second organic solvent in the presence of an organic base to synthesize (2-chloroethylmethylene)cyclolxane (IV). Then (2-chloroethylmethylene)cyclohexane (IV) and urotropine are subjected to quaternization in a third organic solvent to synthesize N-cyclohexylidene ethyl urotropine hydrochloride (V). Finally, the N-cyclohexylidene ethyl urotropine hydrochloride (V) undergoes hydrolysis and rearrangement reaction in a solvent in the presence of an inorganic mineral acid to synthesize 2-(1-cyclohexenyl)ethylamine (I).

Claims15

Dependent claims

A method for synthesizing 2-(1-cyclohexenyl)ethylamine of formula (I):

the method comprising:
(1) reacting cyclohexanone (II) with a Grignard reagent in a first organic solvent to produce 1-vinylcyclohexanol (III);
(2) subjecting 1-vinylcyclohexanol (III) to chlorination and rearrangement reaction with a chlorinating reagent in a second organic solvent in the presence of an organic base to synthesize (2-chloroethylmethylene)cyclohexane (IV);
(3) subjecting (2-chloroethylmethylene)cyclohexane (IV) and urotropine to quaternization in a third organic solvent to synthesize N-cyclohexylidene ethyl urotropine hydrochloride (V);
and
(4) subjecting the N-cyclohexylidene ethyl urotropine hydrochloride (V) to hydrolysis and rearrangement in a solvent in the presence of an inorganic mineral acid to produce 2-(1-cyclohexenyl)ethylamine (I);
as shown in the following scheme:

4 more elements

Dependencies are inferred from the claim text.

Facts

Application: 16/953,317Filed 19 Nov 2020
Priority: CN 202010628038.91 Jul 2020
Published: US 2022/0002224 A16 Jan 2022
Granted: 12 Apr 2022
Term ends: Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07C 29/40
By reaction with aldehydes or ketones: with compounds containing carbon-to-metal bonds
C07C 209/62
Preparation of compounds containing amino groups bound to a carbon skeleton: by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or…
C07C 17/013
Preparation of halogenated hydrocarbons: by addition of halogens
C07C 17/16
By replacement by halogens: of hydroxyl groups

Family

US 2022/0002224 A1Pre-grant publication · published 6 Jan 2022
US 11,299,451 B2This patent

From the US filing history. Foreign family members aren’t listed.

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