1H-Indole-3-MethanaMine, 7-chloro-N,N-diMethyl- synthesis
- Product Name:1H-Indole-3-MethanaMine, 7-chloro-N,N-diMethyl-
- CAS Number:159503-76-1
- Molecular formula:C11H13ClN2
- Molecular Weight:208.69
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Yield: 86%
Reaction Conditions:
with formaldehyd in acetic acid at 20; for 16.1667 h;
Steps:
16.1
We added dimethyl amine (2.05 mL, 16.3 mmol., 40% solution) to a mixture of acetic acid (13.6 mL) and formaldehyde (0.340 mL, 4.5 mmol, 37% solution) under argon. We stirred the reaction mixture for 10 minutes and then treated it with 7-chloroindole (1-1) (604 mg, 4.0 mmol). We stirred the resulting mixture at room temperature for - 16 hours. We first neutralized the reaction mixture with K2CO3, then basified it with NaOH (2N)5 and then extracted it in ethyl acetate, washed with water, dried, and concentrated. We recrystallized obtained solid from ethyl acetate and hexane to give (1-2): yield 86%, mp 1360C - 138°C, 1H NMR (500 MHz, CDCl3): 2.27(s, 6H), 3.61 (s, 2H), 7.04 (dd, J = 8.0 and 8.0 Hz5 IH), 7.15 (d, J = 2.5 Hz, IH), 7.18 (d, J = 7.5 Hz, IH), 7.60 (d, J = 7.5 Hz, IH), 8.53 (s, IH).
References:
PRESIDENT AND FELLOWS OF HARVARD COLLEGE;THE BRIGHAM AND WOMEN'S HOSPITAL, INC. WO2007/75772, 2007, A2 Location in patent:Page/Page column 122
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