Abstract
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.