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Synthesis of 4‐(4‐Alkyl‐2‐morpholinyl)indoles
Author(s) -
Clark Robin D.
Publication year - 1983
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570200545
Subject(s) - chemistry , sodium borohydride , ketone , alkyl , aluminum hydride , halogenation , lithium (medication) , organic chemistry , sodium hydride , medicinal chemistry , catalysis , medicine , endocrinology , methoxide
N ‐substituted 4‐(2‐morpholinyl)indoles were prepared from 1‐( t ‐butoxycarbonyl)‐4‐acetylindole (7) which was itself prepared from 4‐cyanoindole. Bromination of ketone 7, followed by reaction with amines and subsequent sodium borohydride reduction, gave amino alcohols. These were converted to α‐chloro amides that were cyclized to lactams. Lithium aluminum hydride reduction served both to remove the t ‐BOC protecting group and to reduce the lactams to the 4‐(2‐morpholinyl) indoles.