Borane → HCID 21428691, compound

Participants

Reaction Steps

60 ml. of a 1M solution of boron trihydride in tetrahydrofuran are added dropwise to a stirred solution of 7.0 g of 1-(indol-3-ylglyoxyloyl)-4-(p-chlorophenoxy)piperidine in 135 ml. of tetrahydrofuran under nitrogen. The solution is stirred at ambient temperature for 18 hours and the tetrahydrofuran is removed under reduced pressure to give a white boron complex. The complex is destroyed by refluxing in 135 ml. of methanol with a few drops of glacial acetic acid. After cooling, the methanol is removed under reduced pressure to give a yellow oil. The oil is dissolved in ether, the ether is washed with water, dried and removed under reduced pressure to give a yellow oil. After standing under vacuum for a week, the oil crystallizes to a yellow solid. The solid is recrystallized from toluene and then from an ethanol and water mixture to give white crystals of 3-{2-[4-(p-chlorophenoxy)piperidyl]ethyl}indole, m.p. 132°-133° C.

Provenance & Evidence