Synthesis of n,n-dimethyltryptamine-type compounds, methods, and uses

A method of synthesizing a compound of Formula II:

• wherein:
• each xH is protium;
• n is selected from 1, 2, 3 or 4;
• R1 is independently selected from —R3, —OR3, —O(CO)R3, —F, —Cl, —Br or —I;
• and
• R2 and R3 are independently selected from C1-C4alkyl;
• the method comprising:
• reacting a compound of Formula I:
• with two or more coupling agents to produce an activated compound, the two or more coupling agents comprising:
• a carbodiimide selected from the group consisting of diisopropylcarbodiimide (DIC), (N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide (EDC) and 1-cyclohexyl-(2-morpholinoethyl)carbodiimide metho-p-toluene sulfonate (CMCT), and
• an additive coupling agent selected from the group consisting of 1-hydroxybenzotriazole, hydroxy-3,4-dihydro-4-oxo-1,2,3-benzotriazine, N-hydroxysuccinimide, 1-hydroxy-7-aza-1H-benzotriazole, ethyl 2-cyano-2-(hydroximino)acetate and 4-(N,N-Dimethylamino)pyridine;
• reacting the activated compound with an amine having the formula (R2)2NH to produce a compound of Formula II:
• reacting the compound of Formula II with between about 0.8 and about 1.0 equivalents of LiAlH4 and/or LiAlD4 to produce a compound of Formula III;
• and
• optionally reacting the compound of Formula III with an acidic reagent to produce a pharmaceutically acceptable salt of the compound of Formula III.