Hydrogen Bromide → 3-(3-Hydroxyphenyl)-1-propyl-2-piperidone

Participants

Reaction Steps

The product of Example 8 (10.5 g, 33.4 mM) in dichloromethane (70 ml) was treated with 48% hydrogen bromide in acetic acid (ca 0.5 ml). After 16 h the solvent was evaporated under reduced pressure and the residue was partitioned between chloroform and water. The organic phase was dried and evaporated and the residue was chromatographed on alumina (neutral, grade 3) using 4% methanol in chloroform as eluant. The appropriate fractions were avaporated and recrystallised from ether to yield the title compound (6.8 g) m.p. 61°-3° (Found: C, 71.9; H, 7.8; 5.6% C14H19NO2 requires C, 72.1; H, 8.2; 6.0%).

Provenance & Evidence