Synthesis and structure of 4-hy-droxy- N -iso-propyl-tryptamine (4-HO-NiPT) and its precursors

The title compound, 4-hy-droxy- -iso-propyl-tryptamine ( ) or 4-HO-NiPT (systematic name: 3-{2-[(propan-2-yl)amino]-eth-yl}-1 -indol-4-ol), C H N O, was synthesized in three steps from 4-benzyl-oxyindole ( ) (systematic name: 4-phen-oxy-1 -indole), C H NO. ( ) was treated with oxalyl chloride and is...

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Published in:Acta crystallographica. Section E, Crystallographic communications Crystallographic communications, 2023-03, Vol.79 (Pt 4), p.280-286
Main Authors: Laban, Uroš, Naeem, Marilyn, Chadeayne, Andrew R, Golen, James A, Manke, David R
Format: Article
Language:English
Subjects:
Research Communications
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Summary:The title compound, 4-hy-droxy- -iso-propyl-tryptamine ( ) or 4-HO-NiPT (systematic name: 3-{2-[(propan-2-yl)amino]-eth-yl}-1 -indol-4-ol), C H N O, was synthesized in three steps from 4-benzyl-oxyindole ( ) (systematic name: 4-phen-oxy-1 -indole), C H NO. ( ) was treated with oxalyl chloride and iso-propyl-amine to produce -isopropyl-4-benz-yloxy-3-indole-glyoxyl-amide ( ) {systematic name: 2-[4-(benz-yloxy)-1 -indol-3-yl]-2-oxo- -(propan-2-yl)acet-amide}, C H N O . ( ) was reduced to generate 4-benz-yloxy- -iso-propyl-tryptamine or 4-HO-NiPT, which was characterized as its chloride salt 4-benz-yloxy- -iso-propyl-tryptammonium chloride ( ) (systematic name: {2-[4-(benz-yloxy)-1 -indol-3-yl]eth-yl}(propan-2-yl)aza-nium chloride), C H N O·Cl. Finally the benzyl group of was removed hydrogenation to generate 4-HO-NiPT. The crystal structures of the title compound and all three synthetic precursors are presented.
ISSN:2056-9890
2056-9890
DOI:10.1107/S2056989023002098