Ammonium Acetate → 4-Amino-N-octyloxy-2,2,6,6-tetramethylpiperidine

Participants

Reaction Steps

4-Amino-N-octyloxy-2,2,6,6-tetramethylpiperidine (16.7 g, 62%) is prepared from N-octyloxy-4-oxo-2,2,6,6-tetramethylpiperidine (95.4 mmol, 27.0 g) by the same method as described above, with the exception of the addition of ammonium acetate (954.5 mmol, 73.5 g), 15 g molecular sieves (10−10 m) and 95% NaBH3CN (95.4 mmol, 6.32 g). 1H-NMR (CDCl3); δ=3.61 (t, J=6.6 Hz, 2H, CH2—O), 2.99 (m, 1H, NH2—CH), 1.63 (d, J=11.4 Hz, 2H, NH2), 1.46 (m, 4H, CH2—CH3), 1.26 (m, 12H), 1.15 (s, 6H, CH3), 1.12 (s, 6H, CH3), 0.87 (t, J=7.4 Hz, 3H, CH2—CH3); 13C-NMR (CDCl3): δ=77.0, 59.8, 50.1, 41.4, 33.2, 31.8, 29.6, 29.2, 28.6, 26.4, 21.3, 21.4, 14.1.

Provenance & Evidence