4-methyl-morpholine in N,N-dimethyl-formamide T=-20°C; 2 h; Yield given;

1: N-methylmorpholine / dimethylformamide / 0.03 h / -20 °C 2: N-methylmorpholine, hexamethylphosphoric acid triamide / dimethylformamide / 2 h / -20 °C 3: 89 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 4: N-methylmorpholine / dimethylformamide / 2 h / -20 °C 5: 95 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 6: N-methylmorpholine / dimethylformamide / 2 h / -20 °C View Scheme

1: N-methylmorpholine / dimethylformamide / 0.03 h / -20 °C 2: N-methylmorpholine / dimethylformamide / 2 h / -20 °C 3: 95 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 4: N-methylmorpholine, hexamethylphosphoric acid triamide / dimethylformamide / 2 h / -20 °C 5: 89 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 6: N-methylmorpholine / dimethylformamide / 2 h / -20 °C 7: 95 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 8: N-methylmorpholine / dimethylformamide / 2 h / -20 °C View Scheme

1: N-methylmorpholine / dimethylformamide / 0.03 h / -20 °C 2: N-methylmorpholine / dimethylformamide / 2 h / -20 °C 3: 87 percent / NH3 / methanol / 20 h / Ambient temperature 4: 90 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 5: N-methylmorpholine / dimethylformamide / 2 h / -20 °C 6: 95 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 7: N-methylmorpholine, hexamethylphosphoric acid triamide / dimethylformamide / 2 h / -20 °C 8: 89 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 9: N-methylmorpholine / dimethylformamide / 2 h / -20 °C 10: 95 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 11: N-methylmorpholine / dimethylformamide / 2 h / -20 °C View Scheme

1: 87 percent / NH3 / methanol / 20 h / Ambient temperature 2: 90 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 3: N-methylmorpholine / dimethylformamide / 2 h / -20 °C 4: 95 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 5: N-methylmorpholine, hexamethylphosphoric acid triamide / dimethylformamide / 2 h / -20 °C 6: 89 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 7: N-methylmorpholine / dimethylformamide / 2 h / -20 °C 8: 95 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 9: N-methylmorpholine / dimethylformamide / 2 h / -20 °C View Scheme

1: N-methylmorpholine / dimethylformamide / 2 h / -20 °C 2: 95 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 3: N-methylmorpholine, hexamethylphosphoric acid triamide / dimethylformamide / 2 h / -20 °C 4: 89 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 5: N-methylmorpholine / dimethylformamide / 2 h / -20 °C 6: 95 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 7: N-methylmorpholine / dimethylformamide / 2 h / -20 °C View Scheme

1: 95 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 2: N-methylmorpholine, hexamethylphosphoric acid triamide / dimethylformamide / 2 h / -20 °C 3: 89 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 4: N-methylmorpholine / dimethylformamide / 2 h / -20 °C 5: 95 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 6: N-methylmorpholine / dimethylformamide / 2 h / -20 °C View Scheme

1: N-methylmorpholine, hexamethylphosphoric acid triamide / dimethylformamide / 2 h / -20 °C 2: 89 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 3: N-methylmorpholine / dimethylformamide / 2 h / -20 °C 4: 95 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 5: N-methylmorpholine / dimethylformamide / 2 h / -20 °C View Scheme

1: 89 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 2: N-methylmorpholine / dimethylformamide / 2 h / -20 °C 3: 95 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 4: N-methylmorpholine / dimethylformamide / 2 h / -20 °C View Scheme

1: N-methylmorpholine / dimethylformamide / 2 h / -20 °C 2: 95 percent / 1 N HCl / acetic acid / 0.5 h / Ambient temperature 3: N-methylmorpholine / dimethylformamide / 2 h / -20 °C View Scheme