PMGB

A mixture of 2-((1-benzylpiperidin-4-yl)methyl)-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one (3.4 g, 0.009 mol), sodium ethanethiolate (3.8 g, 0.045 mol) in 34 mL DMF was heated at 50 oC for overnight (12 h). The reaction mixture was cooled to rt and diluted with water (100 mL) and ethyl acetate (100 mL). The unreacted starting material was separated by extracting into the organic layer  using 2 x 100 mL ethyl acetate. The pH of the aqueous layer was adjusted to pH = 7 by carefully adding 1 mL of saturated aqueous citric acid solution. A oil gets separated which soon becomes a white solid. The solid was filtered off, washed with water, redissolved in dichloromethane, dried over sodium sulfate to give 2-((1-benzylpiperidin-4-yl)methyl)-6-hydroxy-5-methoxy-2,3-dihydro-1H-inden-1-one as a white solid (2.4 g, 74% yield). NMR complies.

Ref. WO 2008/073452 A1, US 2008/0153878 A1

A mixture of 1-phenylethanol (1.21 mL) and 48% HBr in water (12 mL) was stirred at room temperature for overnight (12 h). The reaction mixture was diluted with 50 mL ethyl acetate, washed with 50 mL aqueous saturated NaHCO₃ solution, dried over Na₂SO₄ and evaporated under reduced pressure to give (1-bromoethyl)benzene as a light brown oil (1.5 g, 83% yield). NMR complies.

This material was prepared to protect the N atom of an amide so that after a sequence of reactions it can be cleaved off easily using MsOH. [06TL1813]