ChemicalBook CAS DataBase List N,N-DIMETHYL-5-NITROTRYPTAMINE

N,N-DIMETHYL-5-NITROTRYPTAMINE synthesis

5synthesis methods

Product Name:N,N-DIMETHYL-5-NITROTRYPTAMINE
CAS Number:69937-13-9
Molecular formula:C12H15N3O2
Molecular Weight:233.27

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Yield:69937-13-9 92%

Reaction Conditions:

with dimethyl amine in ethanol;

Steps:

14 5-Nitro-3-[2-(dimethylamino)ethyl]indole (3)

EXAMPLE 14 5-Nitro-3-[2-(dimethylamino)ethyl]indole (3) Into 50 mL of absolute ethanol cooled at 0° C. was bubbled dimethylamine for 30 min. To this solution was added a solution of 5-nitro-3-(2-bromoethyl)indole (0.50 g, 1.86 mmol) in 50 mL of absolute ethanol and the mixture was transferred to a pressure vessel and heated at 80° C. for 2 h. The cooled mixture was then evaporated and the residue was partitioned between 1N NaOH and ethyl acetate. The organic phase was separated, washed (brine), dried (Na₂ SO₄) and evaporated to give the title compound (0.40 g, 92%) as a yellow solid, mp 132°-135° C.: IR (neat) 1330 cm^-1; ¹ H NMR (CDCl₃, 200 MHz) δ9.23 (s, 1H), 8.54 (s, 1H), 7.98 (d, J=8.8 Hz, 1H), 7.26-7.10 (m, 2H), 2.98 (m, 2H), 2.71 (m, 2H), 2.37 (s, 6H).

References:

US5382592,1995,A