N,N-dimethyl-1-piperidin-4-ylethanamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following general procedure B, 6-bromo-4-chloro-3-(methylsulfonyl)quinoline (100 mg, 0.311 mmol) was reacted with N,N-dimethyl-1-(piperidin-4-yl)ethanamine (229 mg, 1.00 mmol) to afford the desired product (93 mg, 68%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 9.24 (s, 1H), 8.50 (d, J=1.5 Hz, 1H), 8.11-7.93 (m, 2H), 3.67-3.55 (m, 2H), 3.44 (s, 3H), 3.34 (s, 2H), 2.75-2.62 (m, 1H), 2.46 (s, 6H), 2.07-1.96 (m, 1H), 1.90 (d, J=12.3 Hz, 2H), 1.73-1.53 (m, 2H), 1.15 (d, J=6.6 Hz, 3H).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following general procedure B, (6-bromo-4-chloroquinolin-3-yl)(cyclopropyl)methanone (300 mg, 0.965 mmol) was reacted with N,N-dimethyl-1-(piperidin-4-yl)ethanamine (332 mg, 1.45 mmol) to afford the desired product (264 mg, 63%) as a yellow solid: 1H NMR (300 MHz, CD3OD) δ 8.78 (s, 1H), 8.32 (s, 1H), 7.95-7.80 (m, 2H), 3.57-3.39 (m, 2H), 3.21 3.05 (m, 2H), 2.59-2.42 (m, 2H), 2.31 (s, 6H), 2.11-1.97 (m, 1H), 1.89 (d, J=12.4 Hz, 1H), 1.80-1.67 (m, 1H), 1.68-1.49 (m, 2H), 1.36-1.16 (m, 4H), 1.06 (d, J=6.6 Hz, 3H).