Sodium Hydroxide → HCID 22729078, compound

Participants

Reaction Steps

1-(4-Hydroxy-4-naphthalen-2-yl-piperidin-1-yl)ethanone (3.40 g, 13 mmol) was dissolved in hydrochloric acid (50 ml, 6M) and the solution refluxed for 12 hours. The resultant mixture was cooled in ice, basified with sodium hydroxide solution (32 ml, 10M) and extracted with dichloromethane (2×100 ml). The extracts were combined, dried (MgSO4) and concentrated to give 4-naphthalen-2-yl-1,2,3,6-tetrahydropyridine (2.12 g, 78% ) as a tan solid; δH (CDCl3) 2.60 (2H, m, tetrahydropyridinyl CH2), 3.20 (2H, t, J 5.6 Hz, tetrahydropyridinyl CH2), 3.60 (2H, m, tetrahydropyridinyl CH2), 6.30 (1H, m, CH=CR), 7.45 (2H, m, ArH), 7.60 (1H, dd, J 8.4, 1.4 Hz, ArH), and 7.80 (4H, m, ArH).

Provenance & Evidence