Grmph, this article is on Lego's harddisk for almost a year......
We need reference 3 as soon as possible, otherwise sleep will be hard to find!
Reduction of nitroalkanes 6 and 8 to the amines 7 or 9:
A suspension of 10-20 g LiAlH4 in 250-350 ml THF and 30-100 ml dioxane is heated to reflux. A solution of 50 mmol nitroalkane in 100-150 ml THF or dioxane is added dropwise and the solution is refluxed for further 5-8 h. After careful addition of water to the ice-cooled reaction mixture the formed precipitate is removed by filtration and refluxed for 2 h with ether. The pooled filtrates were dried over potassium carbonate and evaporated on a rotary evaporator. The mono- or dihydrochlorides, hydrogenoxalates or pikrates were synthesized in the usual manner, the m.p. or decomposition points are given in table 2 and data of the elemental analysis in table 3. The yields given in table 2 are isolated ammonium salts, based on used nitroalkane 6 or 8. [...]
2-(2,5-Dimethoxyphenyl)-N4,N4-dimethyl-1,4-butandiamine (7b):
A solution of 14.8 g (50 mmol) 3-(2,5-dimethoxyphenyl)-N,N-dimethyl-4-nitrobutyramid (6b)3 in 100 ml dioxane was added over a period of 30 min to a refluxing solution of 19 g LiAlH4, 350 ml THF and 50 ml dioxane. After 8 h of reflux the solution is hydrolysed with 75 ml while cooled with ice and worked-up as described above. 8.4 of a yellow oil are obtained which is dissovled in ether and a saturated solution of HCl in ether is added dropwise. Yield of dihydrochloride: 10.8 g (67%); m.p. 149-151 °C (EtOH/ether)
Bufotenine (10):
3.25 g (10 mmol) of 7b dihydrochlorid were heated to reflux with 48% HBr for 30 min in a inert gas atmosphere. The solution was diluted with 90 ml water and evaporated to dryness. The aqeuous solution of the residue was heated to reflux with activated carbon and evaporated. The residue is dried until no more weight is lost over P4O10 and NaOH in an evacuated descicator.
To the solution of the hydroquinone derivative (3.8 g) in 120 ml water a solution of 6.4 g K3Fe(CN)6 and 3.3 g NaHCO3 in 120 ml are added dropwise over a period of 10 min. After 30 min a very little amount of sodium dithionite is added. After removal of the precipitate by filtration the solution is extracted for 2 days with ether which is free of peroxides not sure if '2 d' really means 2 days or perhaps it is a typo and should read '2 x', whatever, extract with ether
The amorphous residue of the etheral solution consists of almost pure 10 (1.1 g, 54%), which could be purified by sublimation at 140 °C/10-4 Torr, m.p. 139 °C (lit. 15 143 °C).
3 D. Seebach, H. F. Leitz and V. Ehrig, Chem. Ber. 108, 1924 (1975) and literature cited therein