This question was originally posted by Psyloxy. The reason for me to post it again is to get the picture WHY it doesn´t work.
Gramine, 3-(dimethylaminomethyl)indole,
R-CH2-N-(CH3)2, can be made in this extremly easy fashion:
All the following are cooled in an ice bath.
12.33g 53%(aq)dimethylamine, 20ml glacial acetic acid, and 11g 37%formaldehyde. To this is 16.8g indole added. An exothermic reaction results as the indole dissolves. After several hours the solution is made alkaline with (aq)NaOH. The mass crystallizes and is suction filtred, washed and dried. Approximately 25g gramine is obtained.
Fucking hey! That´s a pretty good yield(God I wish other things were produced in this easy and high-yielding way)
Now if someone for some naughty reason would like to have that alkyl chain one carbon longer. R-CH2-CH2-N-(R')2. Could it be so freaking simple as to just use acetaldehyde instead of formaldehyde? Of course not. But why? That´s finally the question.
Strontium