C-(2-METHYL-1H-INDOL-5-YL)-METHYLAMINE synthesis

7synthesis methods

Product Name:C-(2-METHYL-1H-INDOL-5-YL)-METHYLAMINE
CAS Number:36798-25-1
Molecular formula:C10H12N2
Molecular Weight:160.22

36798-24-0 Synthesis

36798-24-0
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36798-25-1
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Yield:36798-25-1 97%

Reaction Conditions:

Stage #1: 2-methyl-1H-indole-5-carbonitrilewith lithium aluminium tetrahydride in tetrahydrofuran at 5 - 7; for 1.5 h;Reflux;
Stage #2: with water;sodium hydroxide in tetrahydrofuran; for 0.166667 h;Cooling with ice;

Steps:

1.2

LiAlH₄(9.70 g, 255 mmol) was suspended in THF (400 mL) and the resulting suspension was cooled in a ice/water bath. A solution of 2-methyl-1H-indole-5-carbonitrile (11.4 g, 73 mmol) in THF (100 mL) was added dropwise over 30 minutes while keeping the internal temperature at 5-7° C. The mixture was then heated to reflux for 1 h. The mixture was cooled in an ice-water bath. To this mixture was sequentially added 20 ml water, 10 ml sodium hydroxide-solution (5M) and 50 ml water and the mixture was stirred for 10 minutes. A generous amount of MgSO₄was added. The mixture was stirred for additional 10 minutes and then filtered. The residue was thoroughly extracted with THF. To the combined filtrates was added EtOAc (1 L) and this solution was dried with MgSO₄. The mixture was filtered and evaporated to dryness to give the title compound as a light-yellow powder (11.9 g, 97%).1H NMR (500 MHz, DMSO) δ 10.76 (s, 1H), 7.31 (s, 1H), 7.18 (d, J=8.2 Hz, 1H), 6.95 (d, J=8.2 Hz, 1H), 6.05 (s, 1H), 3.73 (s, 2H), 2.36 (s, 3H).

References:

US2012/252853,2012,A1 Location in patent:Page/Page column 13-14