Method for deuteration of an inert methylene

• US 7,126,023 B2
• Filed: 11/12/2002
• Issued: 10/24/2006
• Est. Priority Date: 06/06/2002
• Status: Expired due to Fees

• Current Assignee: WAKO Pure Chemical Industries Limited (Fujifilm Holdings Corporation)
• Original Assignee: WAKO Pure Chemical Industries Limited (Fujifilm Holdings Corporation)
• Inventors: Sajiki, Hironao, Hirota, Kosaku
• Primary Examiner(s): Zucker, Paul A.
• Application Number:
  US10/516,638
• Publication Number:
  US 20050177015A1
• Time in Patent Office: 1,442 Days
• Field of Search: None
• US Class Current: 560/105
• CPC Class Codes: C07B 59/00 Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
• CPC Class Codes: C07B 59/001 Acyclic or carbocyclic compounds
• CPC Class Codes: Y10S 585/941 Isotope exchange process

Abstract

The present invention relates to a method for deuteration of an inert alkane using activated palladium carbon. The present invention discloses

“A method for deuteration of a hydrogen atom of a methyl group or a hydrogen atom bonded to a carbon atom at benzyl position and the other carbon atoms of an alkylene group having not less than 2 carbon atoms, in a compound containing the methyl group or the-alkylene group having not less than 2 carbon atoms, directly bonded to an aromatic ring which may have a substituent, which comprises placing said compound in a deuterated solvent in the presence of activated palladium carbon, under sealed reflux condition”.

Claims

1. A method for replacing with deuterium a hydrogen atom of a methyl group or a hydrogen atom bonded to a carbon atom at a benzyl position and the other carbon atoms of an alkylene group having not less than 2 carbon atoms, in a compound containing the methyl group or the alkylene group having not less than 2 carbon atoms, directly bonded to an aromatic ring which may have a substituent, which comprises placing said compound in a deuterated solvent in the presence of activated palladium carbon, under sealed reflux condition.

2. The method for replacing with deuterium according to claim 1, wherein said compound containing the methyl group or the alkylene group having not less than 2 carbon atoms, directly bonded to the aromatic ring which may have the substituent is a compound having said methyl group.

3. The method for replacing with deuterium according to claim 1, wherein said compound containing the methyl group or the alkylene group having not less than 2 carbon atoms, directly bonded to the aromatic ring which may have the substituent, is a compound containing said alkylene group having not less than 2 carbon atoms, directly bonded to the aromatic ring which may have a substituent.

4. The method for replacing with deuterium according to claim 1, wherein said compound containing the methyl group or the alkylene group having not less than 2 carbon atoms, directly bonded to the aromatic ring, in said compound containing the methyl group or the alkylene group having not less than 2 carbon atoms, directly bonded to the aromatic ring which may have the substituent, is a compound represented by the general formula [1]:

5. The method for replacing with deuterium according to claim 4, wherein the alkylene group having not less than 2 carbon atoms, represented by A is a straight chained alkylene group and X is a hydrogen atom, a carboxyl group, an acyl group, an acylamino group or an alkoxycarbonyl group.

6. The method for replacing with deuterium according to claim 4, wherein the alkylene group having not less than 2 carbon atoms, represented by A is a straight chained alkylene group having not less than 3 carbon atoms and X is an alkoxy group, a hydroxyl group or an amino group.

7. The method for replacing with deuterium according to claim 1, wherein the substituent, which an aromatic ring may have, is one selected from the group consisting of an alkyl group, an aryl group, an aralkyl group, an alkoxy group, a nitro group and an amino group.