Method of Deuteration Using Mixed Catalyst

• US 20080234488A1
• Filed: 12/21/2004
• Published: 09/25/2008
• Est. Priority Date: 01/23/2004
• Status: Active Grant

• Current Assignee: FUJIFILM Wako Pure Chemical Corporation (Fujifilm Holdings Corporation)
• Original Assignee: WAKO Pure Chemical Industries Limited (Fujifilm Holdings Corporation)
• Inventors: Ito, Nobuhiro, Sajiki, Hironao, Hirota, Kosaku, Maesawa, Tsuneaki, Muto, Kazushige
• Granted Patent: US 9,255,070 B2
• Time in Patent Office: Days
• US Class Current: 546/304
• CPC Class Codes: C07B 2200/05 Isotopically modified compounds, e.g. labelled
• CPC Class Codes: C07B 59/00 Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
• CPC Class Codes: C07C 209/68 from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
• CPC Class Codes: C07C 37/00 Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 39/06 Alkylated phenols
• CPC Class Codes: C07C 51/353 by isomerisation; by change of size of the carbon skeleton
• CPC Class Codes: C07C 57/30 containing six-membered aromatic rings
• CPC Class Codes: C07C 63/04 Monocyclic monocarboxylic acids
• CPC Class Codes: C07D 213/74 Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
• CPC Class Codes: C07D 213/80 in position 3

Abstract

The subject of the present invention is to provide a method for deuteration, which can obtain a compound having an aromatic ring and/or a heterocyclic ring at an improved deuteration ratio. The present invention relates to a method for deuteration of a compound having an aromatic ring and/or a heterocyclic ring, comprising reacting the compound having an aromatic ring and/or a heterocyclic ring with a heavy hydrogen source in the presence of an activated mixed catalyst of not less than two kinds of catalysts selected from among a palladium catalyst, a platinum catalyst, a rhodium catalyst, an iridium catalyst, a ruthenium catalyst, a nickel catalyst and a cobalt catalyst.

Claims

1. A method for deuteration of a compound having an aromatic ring and/or a heterocyclic ring, comprising reacting the compound having an aromatic ring and/or a heterocyclic ring with a heavy hydrogen source in the presence of an activated mixed catalyst of not less than two kinds of catalysts selected from among a palladium catalyst, a platinum catalyst, a rhodium catalyst, an iridium catalyst, a ruthenium catalyst, a nickel catalyst and a cobalt catalyst.

2. The method for deuteration according to claim 1, wherein the heavy hydrogen source is a deuterated solvent.

3. The method for deuteration according to claim 2, wherein the deuterated solvent is heavy water (D₂O).

4. The method for deuteration according to claim 1, wherein the activated mixed catalyst is a catalyst obtained by activating a mixed catalyst of not less than two kinds of catalysts selected from among a non-activated palladium catalyst, platinum catalyst, rhodium catalyst, iridium catalyst, ruthenium catalyst, nickel catalyst and cobalt catalyst by contact with hydrogen gas or heavy hydrogen gas.

5. The method for deuteration according to claim 4, wherein the contact of the non-activated mixed catalyst with hydrogen gas or heavy hydrogen gas is carried out in a reaction system of the deuteration.

6. The method for deuteration according to claim 1, wherein the activated mixed catalyst is an activated mixed catalyst of a palladium catalyst and a platinum catalyst.

7. The method for deuteration according to claim 6, wherein the palladium catalyst is palladium carbon.

8. The method for deuteration according to claim 6, wherein the platinum catalyst is platinum carbon.

9. The method for deuteration according to claim 6, wherein the activated mixed catalyst of a palladium catalyst and a platinum catalyst has a weight ratio of each metal in the palladium catalyst and the platinum catalyst of 1:

99 to 99;

1.

10. The method for deuteration according to claim 1, wherein the compound having an aromatic ring and/or a heterocyclic ring has an alkylene chain bonded to the aromatic ring or the heterocyclic ring.

11. The method for deuteration according to claim 1, wherein the compound having an aromatic ring and/or a heterocyclic ring has an alkylamino group bonded to the aromatic ring or the heterocyclic ring.

12. The method for deuteration according to claim 1, wherein the compound having an aromatic ring and/or a heterocyclic ring has a carboxyl group bonded to the aromatic ring or the heterocyclic ring.