Abstract
AbstractTreatment of cis‐ and trans‐10‐hydroxy‐N‐methyl‐decahydroisoquinoline, (3a) and (10a) respectively, or N‐methyl‐Δ9,10‐octahydroisoquinoline (4 a) with hydrogen chloride in acetic acid affords the thermodynamically more stable trans‐isomer of 10‐chloro‐N‐methyl‐decahydroisoquinoline (1a). On the other hand ring closure of β‐(cyclohexen‐1‐yl)‐ethylamines 11a or 11b with aqueous formaldehyde in the presence of chloride ions leads to the 10‐cis‐chlorides 2a or 2b in a kinetically controlled reactions.
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