Organic Chemistry of Drug Synthesis. Volume 7

Reductive amination of 177 via the aldehyde group in the phenoxy acid
178 affords 179.^26
At least several weeks administration of virtually all antidepressant
drugs, be they the classical tricyclic compounds or the newer selective ser-
otonin reuptake inhibitors (SSRI), is required before patients see relief from
their symptoms. A recently developed SSRI whose structure departs mark-
edly from existing agents appears to differ from other agents, in that it
appears to act in a much shorter time. The final step in the synthesis of
this agentelzasonan ( 182 ) comprises aldol condensation of the benz-
aldehyde ( 180 ) with the thiamorpholine ( 181 ).^27

N

N

CH 3

CH=O

180

+

N

S

Cl

Cl

O

181

LiOH

N

N

CH 3

N

S

Cl

Cl

O

182

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9. Y.W. Hong, Y.N. Lee, H.B. Kim, U.S. Patent 6,252,076 (2001).

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