Process for the preparation of substituted N-(benzyl)cyclopropanamines by imine hydrogenation

Patent metadata

Field	Value
Publication number	US-9260378-B2
Application number	US-201113883241-A
Country	US
Kind code	B2
Filing date	Nov 4, 2011
Priority date	Nov 5, 2010
Publication date	Feb 16, 2016
Grant date	Feb 16, 2016

Abstract

The present invention relates to a process for the preparation of substituted N-(benzyl)cyclopropanamines of the general formula (II) starting from N-[(aryl)methylene]cyclopropanamine derivatives. The present invention further provides the N-[(aryl)methylene]cyclopropanamine derivatives used as starting compounds in this process according to the invention, and their use for the preparation of substituted N (benzyl)cyclopropanamines.

First claim

The invention claimed is:

1. A process for the preparation of N-(benzyl)cyclopropanamines of the general formula (II)

wherein
Z is hydrogen, C 1 -C 8 -alkyl, C 1 -C 4 -haloalkyl or C 3 -C 7 -cycloalkyl,
X 1 is halogen or C 1 -C 8 -haloalkyl having up to 9 identical or different halogen atoms,
X is C 1 -C 8 -alkyl or C 1 -C 8 -haloalkyl having up to 9 identical or different halogen atoms,
n is 1, 2, 3, or 4,
wherein N-[(aryl)methylene]cyclopropanamine compounds of the general formula (I)

in which Z, X, X 1 and n have the meanings given above,
are catalytically hydrogenated.

2. The process according to claim 1 , wherein a hydrogenation catalyst that is used is selected from the group consisting of a precious metal catalyst and a Wilkinson catalyst.

3. The process according to claim 1 , wherein a hydrogenation catalyst that is used is selected from the group consisting of a ruthenium catalyst, a palladium catalyst, a platinum catalyst, a rhodium catalyst, a Raney nickel catalyst, a Raney cobalt catalyst, a Lindlar catalyst, and a Wilkinson catalyst.

4. The process according to claim 2 , wherein the catalyst is used in supported form applied to carbon, activated carbon, aluminium oxide, silicon dioxide, zirconium dioxide, calcium carbonate or titanium dioxide.

5. The process according to claim 3 , wherein the catalyst is used in supported form applied to carbon, activated carbon, aluminium oxide, silicon dioxide, zirconium dioxide, calcium carbonate or titanium dioxide.

6. The process according to claim 1 , wherein the catalyst is used in a concentration of about 0.01% to about 30% by weight.

7. The process according to claim 2 , wherein the catalyst is used in a concentration of about 0.01% to about 30% by weight.

8. The process according to claim 3 , wherein the catalyst is used in a concentration of about 0.01% to about 30% by weight.

9. The process according to claim 4 , wherein the catalyst is used in a concentration of about 0.01% to about 30% by weight.

10. The process according to claim 5 , wherein the catalyst is used in a concentration of about 0.01% to about 30% by weight.

11. A process for the preparation of N-(benzyl)cyclopropanamines of the general formula (II)

wherein
Z is hydrogen, C 1 -C 8 -alkyl, C 1 -C 4 -haloalkyl or C 3 -C 7 -cycloalkyl,
X 1 is halogen or C 1 -C 8 -haloalkyl having up to 9 identical or different halogen atoms,
X is C 1 -C 8 -alkyl or C 1 -C 8 -haloalkyl having up to 9 identical or different halogen atoms,
n is 1, 2, 3, or 4,
wherein, in a first step [process (B)], cyclopropylamine is condensed with carbonyl compounds of the general formula (III)

wherein Z, X, X 1 and n have the meanings given above, and the resulting N-[(aryl)methylene]cyclopropanamine compounds of the general formula (I)

wherein Z, X, X 1 and n have the meanings given above, are catalytically hydrogenated in a second step [process (A)].

12. N-[(Aryl)methylene]cyclopropanamine compounds of the general formula (I)

wherein
Z is hydrogen, C 1 -C 8 -alkyl, C 1 -C 4 -haloalkyl or C 3 -C 7 -cycloalkyl,
X 1 is halogen or C 1 -C 8 -haloalkyl having up to 9 identical or different halogen atoms,
X is C 1 -C 8 -alkyl or C 1 -C 8 -haloalkyl having up to 9 identical or different halogen atoms,
n is 1, 2, 3, or 4.

Assignees

• Lui Norbert
• Moradi Wahed Ahmed
• Muller Thomas Norbert
• Bayer Ip Gmbh

Inventors

• Lui Norbert
• Moradi Wahed Ahmed
• Muller Thomas Norbert

Classifications

• C07C217/56

  with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms · CPC title

• C07C209/52 Primary

  by reduction of imines or imino-ethers (C07C209/24 takes precedence) · CPC title

• C07C213/02

  by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups · CPC title

• C07C251/24

  having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings · CPC title

• C07C217/58

  with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain · CPC title