ChemicalBook CAS DataBase List 6-CHLORO-2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLINEHYDROCHLORIDE

6-CHLORO-2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLINEHYDROCHLORIDE synthesis

4synthesis methods

Product Name:6-CHLORO-2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLINEHYDROCHLORIDE
CAS Number:23046-68-6
Molecular formula:C11H11ClN2
Molecular Weight:206.67

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2-(5-Chloro-1H-indol-3-yl)ethanamine hydrochloride

942-26-7
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6-CHLORO-2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLINEHYDROCHLORIDE

23046-68-6
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Yield:23046-68-6 77%

Reaction Conditions:

in water at 105; for 4 h;Aqueous acetate buffer;

Steps:

15.1

Step 1 : A stirred suspension of 5-chlorotryptamine hydrochloride (8.00 g, 34.6 mmol) and paraformaldehyde (1.04 g, 34.6 mmol) in water (120 mL) was treated with 3 M acetate buffer (17.5 mL) under nitrogen. The mixture was heated at about 105 ⁰C for 4 hours. The reaction mixture was cooled to about room temperature. The product was isolated by crystallization at about 0 ⁰C. The solid was dissolved in MeOH. The solution was basified with IN NaOH and evaporated to dryness. The residue was washed with cold water and dried to yield 2-(5-chloro-lH-indol-3-yl)ethanamine hydrochloride (5.53 g, 77%). ¹H NMR (DMSO-J₆, 400 MHz) δ 10.82 (s, IH), 7.33 (d, J = 2.0 Hz, IH), 7.23 (d, J = 8.6 Hz, IH), 6.94 (dd, J= 8.6 Hz, J = 2.3 Hz, IH), 3.80 (s, IH), 2.92 (t, J = 8.4 Hz, 2H), 2.53 (t, J= 8.6 Hz, 2H), 2.47-2.46 (m, 2H).

References:

WO2009/89454,2009,A1 Location in patent:Page/Page column 95

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