In situ or one-pot hydrogenation and reductive amination...

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

Reexamination Certificate

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C568S448000

Reexamination Certificate

active

07462742

ABSTRACT:
An in situ or one-pot process for the preparation of the compounds of formula (I) uses a compound of general formula (I):and includes:a) the hydrogenation of a nitrile group of the compound of general formula (II):in which R1to R4 are especially H or alkyl and n varies from 0 to 4, in the presence of a hydrogenation catalyst, a methylating agent and an organic acid as solvent, and at a temperature Ta below the initiation temperature of a reductive amination reaction, to give a primary amine from the nitrile group; andb) the reductive amination of the primary amine in the presence of hydrogen, at a temperature Tb above Ta, to give the dimethylated amine of general formula (I) by activation of the methylating age.

REFERENCES:
patent: 5043466 (1991-08-01), Shepard
patent: 6350912 (2002-02-01), Chavan et al.
patent: 2005/0033088 (2005-02-01), Reguri et al.
patent: 0 112 669 (1984-07-01), None
patent: 1 238 965 (2005-06-01), None
patent: WO 02/50017 (2002-06-01), None
Yardley et al., “2-Phenyl-2-(1-hydroxycycloalkyl)ethylamine Derivatives: Synthesis and Antidepressant Activity.”J. Med. Chem.33(1990): 2899-2905.

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