Ammonia → 7-Mesitylenesulfonyl-1,7,13-triazatridecane

Participants

Reaction Steps

Raney nickel (W-2 grade, 2.9 g) and 39 (5.69 g, 15.8 mmol) in concentrated NH4OH (10 mL) and CH3OH (60 mL) were saturated with NH3 as 41. The mixture was shaken with hydrogen at 50-55 psi in a 200 mL Parr bottle for 42 hours. The suspension was filtered through Celite, and the solvents were removed in vacuo. The residue was passed through a short silica gel column (EtOH then 5% concentrated NH4OH/EtOH) to give 5.71 g (98%) of 42 as a light yellow oil: NMR δ 1.17 (m, 4 H), 1.47 (m, 8 H), 2.27 (s, 3 H), 2.57 (s, 6 H), 2.61 (m, 4 H), 3.13 (t, J=7.5, 4 H), 6.91 (s, 2 H); HRMS calcd. for C19H36N3O2S 370.2528 (M+H), found. 370.2530 (M+H).

Provenance & Evidence