Tryptamine → Diisopropylethylamine

HRID 1292369Notes

Reaction equation

HRID 1292369 reaction equation
NCC[C:4]1[C:12]2[C:7](=[CH:8]C=CC=2)[NH:6][CH:5]=1.C(Cl)Cl.C(Cl)(Cl)Cl.O1[CH2:24][CH2:23][CH2:22]C1>N1C=CC=CC=1.C(N(CC)CC)C.C(OCC)C>[CH:23]([N:6]([CH:7]([CH3:12])[CH3:8])[CH2:5][CH3:4])([CH3:24])[CH3:22]

Participants

8

Reactant 4

HCID 1150TryptamineHCID 6212ChloroformHCID 6344DichloromethaneHCID 8028Tetrahydrofuran

Product 1

HCID 81531Diisopropylethylamine

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Procedure

As shown in reaction Scheme B, the 2-aryltryptamine may be condensed with a carboxylic acid of type (6) using the coupling reagent 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC), 1,3-dicyclohexylcarbodiimide (DCC) or the like with or without 1-hydroxybenzotriazole (HOBt) and a tertiary amine base such as N-methylmorpholine (NMM), triethylamine or the like in an inert organic solvent such as methylene chloride, chloroform, dimethylformamide, or mixtures thereof at or near room temperature for a period of 3-24 hours to provide the corresponding amide derivative (7). Alternatively, 2-aryltryptamine (5) can be treated with an active ester or acid chloride of type (8) in an inert organic solvent such as methylene chloride, chloroform, tetrahydrofuran, diethyl ether, or the like and a tertiary amine base such as triethylamine, diisopropylethylamine, pyridine or the like at a temperature of 0°-25° C. for 30 minutes to 4 hours to give (7). ##STR9##

Sources & evidence

ORD record
ord-460a140f472c4a789f9103988a2c828c
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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