piperidine; 4-(N,N-dimethlyamino)pyridine in N,N-dimethyl-formamide T=20°C; Knoevenagel condensation; 192 h; Inert atmosphere;

1: pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 12 h / 0 - 20 °C 2: toluene / 5 h / 60 °C / Inert atmosphere 3: 10 Pd(OH)2 on C; hydrogen / methanol / 36 h / 20 °C 4: piperidine; 4-(N,N-dimethlyamino)pyridine / N,N-dimethyl-formamide / 192 h / 20 °C / Inert atmosphere View Scheme

1.1: caesium carbonate / methanol / pH 7 1.2: 11 h / 0 - 20 °C / Inert atmosphere 2.1: pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 12 h / 0 - 20 °C 3.1: toluene / 5 h / 60 °C / Inert atmosphere 4.1: 10 Pd(OH)2 on C; hydrogen / methanol / 36 h / 20 °C 5.1: piperidine; 4-(N,N-dimethlyamino)pyridine / N,N-dimethyl-formamide / 192 h / 20 °C / Inert atmosphere View Scheme

1: toluene / 5 h / 60 °C / Inert atmosphere 2: 10 Pd(OH)2 on C; hydrogen / methanol / 36 h / 20 °C 3: piperidine; 4-(N,N-dimethlyamino)pyridine / N,N-dimethyl-formamide / 192 h / 20 °C / Inert atmosphere View Scheme

1: 10 Pd(OH)2 on C; hydrogen / methanol / 36 h / 20 °C 2: piperidine; 4-(N,N-dimethlyamino)pyridine / N,N-dimethyl-formamide / 192 h / 20 °C / Inert atmosphere View Scheme

1.1: water; sodium hydroxide / tetrahydrofuran / 0.75 h / 20 °C 2.1: caesium carbonate / methanol / pH 7 2.2: 11 h / 0 - 20 °C / Inert atmosphere 3.1: pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 12 h / 0 - 20 °C 4.1: toluene / 5 h / 60 °C / Inert atmosphere 5.1: 10 Pd(OH)2 on C; hydrogen / methanol / 36 h / 20 °C 6.1: piperidine; 4-(N,N-dimethlyamino)pyridine / N,N-dimethyl-formamide / 192 h / 20 °C / Inert atmosphere View Scheme

1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide; toluene / 12 h / Reflux 2.1: 1H-imidazole / N,N-dimethyl-formamide / 1.5 h / 0 - 20 °C / Inert atmosphere 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 3.2: 13.5 h / 0 - 60 °C / Inert atmosphere 4.1: water; sodium hydroxide / tetrahydrofuran / 0.75 h / 20 °C 5.1: caesium carbonate / methanol / pH 7 5.2: 11 h / 0 - 20 °C / Inert atmosphere 6.1: pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 12 h / 0 - 20 °C 7.1: toluene / 5 h / 60 °C / Inert atmosphere 8.1: 10 Pd(OH)2 on C; hydrogen / methanol / 36 h / 20 °C 9.1: piperidine; 4-(N,N-dimethlyamino)pyridine / N,N-dimethyl-formamide / 192 h / 20 °C / Inert atmosphere View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 1.2: 13.5 h / 0 - 60 °C / Inert atmosphere 2.1: water; sodium hydroxide / tetrahydrofuran / 0.75 h / 20 °C 3.1: caesium carbonate / methanol / pH 7 3.2: 11 h / 0 - 20 °C / Inert atmosphere 4.1: pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 12 h / 0 - 20 °C 5.1: toluene / 5 h / 60 °C / Inert atmosphere 6.1: 10 Pd(OH)2 on C; hydrogen / methanol / 36 h / 20 °C 7.1: piperidine; 4-(N,N-dimethlyamino)pyridine / N,N-dimethyl-formamide / 192 h / 20 °C / Inert atmosphere View Scheme

1.1: 1H-imidazole / N,N-dimethyl-formamide / 1.5 h / 0 - 20 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 2.2: 13.5 h / 0 - 60 °C / Inert atmosphere 3.1: water; sodium hydroxide / tetrahydrofuran / 0.75 h / 20 °C 4.1: caesium carbonate / methanol / pH 7 4.2: 11 h / 0 - 20 °C / Inert atmosphere 5.1: pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 12 h / 0 - 20 °C 6.1: toluene / 5 h / 60 °C / Inert atmosphere 7.1: 10 Pd(OH)2 on C; hydrogen / methanol / 36 h / 20 °C 8.1: piperidine; 4-(N,N-dimethlyamino)pyridine / N,N-dimethyl-formamide / 192 h / 20 °C / Inert atmosphere View Scheme

water; unspecific esterase hydrolysis;