# US 2014/0155629 A1 · Processes for the preparation of enamines

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- Number: US 2014/0155629 A1
- Document ID: US20140155629A1
- Status: Published application
- Kind: A1
- Application number: 14/172,516
- Filed: 2014-02-04
- Published: 2014-06-05
- Earliest claimed: 2010-12-03
- Assignees: Dow AgroSciences LLC
- Inventors: Douglas C. Bland; Todd W. Toyzan
- Web page: https://patentgrep.com/patent/US20140155629A1

## 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 to produce 1-(3-methylsulfanyl-but-1-enyl)-pyrrolidine said process comprising:
(A) reacting, in a reaction zone that comprises solvents, pyrrolidine and 3-methylsulfanyl-butyraldehyde to produce 1-(3-methylsulfanyl-but-1-enyl)-pyrrolidine and H2O, wherein said reacting, in said reaction zone, is conducted under azeotropic distillation conditions comprising
(1) a pressure from about 5000 Pascals (Pa) to about 15,000 Pa, and
(2) a temperature from about 25° C. to about 65° C.; and
wherein said solvents are initially toluene and acetonitrile, and then H2O, where said H2O is produced from the condensation of said pyrrolidine and said 3-methylsulfanyl-butyraldehyde to produce said 1-(3-methylsulfanyl-but-1-enyl)-pyrrolidine, thereby forming a ternary azeotrope of toluene, acetonitrile, and H2O; and
(B) removing a vapor phase from said reaction zone wherein said vapor phase comprises H2O;
wherein said process no desiccants are used to remove H2O;
wherein said process said molar ratio of pyrrolidine to 3-methylsulfanyl-butyraldehyde is greater than 1 but less than about 1.1.