Process for preparation of citalopram and enantiomers

Details Process for preparation of citalopram and enantiomers Process for preparation of citalopram and enantiomers

2011-08-02

2011-08-02

Solola, Taofiq (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

07989645

ABSTRACT:
The present invention provides a process for preparation of 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofuran car-bonitrile comprising reacting a compound of formula IVa, in the presence of a base with a compound of formula RX,wherein R is selected from alkyl, alkenyl, aryl and heteroaryl which may be optionally substituted with electron withdrawing groups and X is selected from F, Cl, Br, I, CN, OTf and OR1, wherein Tf represents trifluoromethanesulfonyl group, and R1is optionally substituted alkyl, Z is a cyano group or a group that may be converted to a cyano group;further wherein RX is selected such that an intermediate ether derivative, a compound of formula Va formed from said reaction cyclizes to a compound of formula VI,and where Z is not a cyano group, conversion of the group Z in the compound of formula VI to a cyano group to form 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofuran carbonitrile. The present invention also provides novel ether compound, a compound of formula Va and a process for preparation thereof.

REFERENCES:
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patent: RE34712 (1994-08-01), Boegesoe et al.
patent: 7112686 (2006-09-01), Humble et al.
patent: 2005/0065207 (2005-03-01), Sommer et al.
patent: WO 03/051861 (2003-06-01), None
patent: WO 2005/047274 (2005-05-01), None

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