Diethyl Ether → {4-[1-(4-Bromo-phenyl)-2,3-dihydro-1H-indol-5-yloxy]-butyl}-diethyl-amine

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Reaction Steps

104 mg (0.25 mmol) {4-[1-(4-Bromo-phenyl)-1H-indol-5-yloxy]-butyl}-diethyl-amine in 1 ml TFA were treated with 32 mg (0.5 mmol) NaCNBH3 at 0° C. for 5 min and 30 min at RT. Ether and water were added, followed by 2M NaOH. The inorganic phase was extracted with ether, the combined organic phases were washed with water and dried over Na2SO4. Column chromatography on silica gel with CH2Cl2/MeOH 19:1-1%sat.NH3 in MeOH yielded 40 mg (38%) {4-[1-(4-Bromo-phenyl)-2,3-dihydro-1H-indol-5-yloxy]-butyl}-diethyl-amine as light yellow waxy solid, MS: 417 (MH+, 1Br).

Provenance & Evidence