1,2-Dibromoethane → N-Propoxy-4-oxo-2,2,6,6-tetramethylpiperidine

Participants

Reaction Steps

N-Propoxy-4-oxo-2,2,6,6-tetramethylpiperidine (3.2 g, 26%) is synthesized in the same manner as described above with regard to N-cyclohexyloxy-4-oxo-2,2,6,6-tetramethylpiperidine, with the exception of the addition of Zn (61.1 mmol, 4.00 g), 1,2-dibromoethane (200 μl), trimethyl-chlorosilane (250 μl), iodopropane (58.8 mmol, 10.0 g), CuCN (53.6 mmol, 4.80 g), LiCl (114 mmol, 4.80 g) and 4-oxo-TEMPO (58.8 mmol, 10.0 g). 1H-NMR (CDCl3): δ=3.78 (t, J=6.7 Hz, 2H, O—CH2), 2.55 (d, J=12.7 Hz, 2H, CH2—CCH3), 2.20 (d, J=12.7 Hz, 2H, CH2—CCH3), 1.57 (m, 2H, CH2—CH3), 1.28 (s, 6H, C—CH3), 1.14 (s, 6H, C—CH3), 0.95 (t, J=7.45 Hz, 3H, CH2—CH3); 13C-NMR (CDCl3): δ208.5, 78.5, 63.0, 53.3, 32.5, 22.5, 21.8, 10.9.

Provenance & Evidence