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ChemicalBook CAS DataBase List 7-BENZYLOXYTRYPTAMINE

7-BENZYLOXYTRYPTAMINE synthesis

5synthesis methods

Product Name:7-BENZYLOXYTRYPTAMINE
CAS Number:31677-75-5
Molecular formula:C17H18N2O
Molecular Weight:266.34

1H-Indole, 3-(2-azidoethyl)-7-(phenylmethoxy)-

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Yield:31677-75-5 95%

Reaction Conditions:

with triphenylphosphine in pyridine;water at 20; for 18 h;

Steps:

79 2-(7-(Benzyloxy)-1H-indol-3-yl)ethylamine

To a solution of 3-(2-azidethyl)-7-(benzyloxy)-1H-indole (5.10 g, 17.4 mmol) in pyridine (100 mL)-water (100 mL) is added triphenylphosphine (5.02 g, 19.1 mmol) under nitrogen atmosphere, and the mixture is stirred at room temperature for 18 hours. The reaction solution is poured into water, and the mixture is extracted with chloroform. The organic layer is washed with a saturated brine, and dried over anhydrous magnesium sulfate. The solvent is evaporated under reduced pressure, and the obtained crude product is purified by silica gel column chromatography (a saturated ammonia solution in chloroform → a saturated ammonia solution in chloroform-methanol = 50:1 → 10: 1) to give the title compound (4.38 g, yield: 95 %). 1H-NMR (CDCl3) δ: 2.89 (2H, t, J=6.8Hz), 3.02 (2H, t, J=6.8Hz), 5.21 (2H, s), 6.73 (1H, d, J=7.7Hz), 7.01 (1H, d, J=2.1Hz), 7.02 (1H, dd, J=8.0, 7.7Hz), 7.24 (1H, d, J=8.0Hz), 7.34-7.43 (3H, m), 7.47-7.49 (2H, m), 8.29 (1H, brs).

References:

EP1514869,2005,A1 Location in patent:Page/Page column 69