# US 2014/0155628 A1 · Processes for the preparation of enamines

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- Number: US 2014/0155628 A1
- Document ID: US20140155628A1
- Status: Published application
- Kind: A1
- Application number: 14/172,443
- Filed: 2014-02-04
- Published: 2014-06-05
- Earliest claimed: 2010-12-03
- Assignees: Dow AgroSciences LLC
- Inventors: Douglas C. Bland; Todd W. Toyzan; Ronald B. Leng; James R. McConnell
- Web page: https://patentgrep.com/patent/US20140155628A1

## CPC

- C07D 295/084: with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The invention disclosed in this document is related to the field of processes for the preparation of enamines wherein R1, R2, R3, R4, R5, and further information are disclosed herein.

## Claims

### Claim 1

A process comprising:
(A) contacting a first mixture with a second mixture in a reaction zone
(1) wherein said first mixture comprises pyrrolidine, and
(2) wherein said second mixture comprises 3-methylsulfanyl-butyraldehyde and toluene, and
(3) wherein said first mixture is contacted with said second mixture below the surface of said second mixture;
(B) reacting in said reaction zone said pyrrolidine and said 3-methylsulfanyl-butyraldehyde to produce 1-(3-methylsulfanyl-but-1-enyl)-pyrrolidine and H2O, wherein said reacting is conducted under azeotropic distillation conditions comprising
(1) a pressure from about 5000 Pa to about 15000 Pa, and
(2) a temperature from about 25° C. to about 65° C.; and
(C) removing a vapor phase comprising toluene and H2O and essentially no 3-methylsulfanyl-butyraldehyde,
wherein the ratio of
(the amount of first mixture added): (the vapor phase removed) is from about
(1 part first mixture added): (3 parts vapor phase removed) to about
(1 part first mixture added): (10 parts vapor phase removed);
wherein said process no desiccants are used to remove H2O in said process; and
wherein said process the molar ratio of amine to carbonyl is greater than 1 but less than about 1.1.