sodium hydroxide; formic acid; acetic anhydride in water; toluene

potassium hydroxide 1) water, 50 deg C, 50 deg C, 20 min; 2) water, room temperature; Yield given. Multistep reaction;

piperidine; acetic acid 2 h; Heating;

1: 1.) sodium hydride / 1) toluene, 70 - 75 deg C, 1 h; 2) touene, 30 deg C, 20 min 2: glacial acetic acid / ethanol / Heating 3: 1.) potassium hydroxide / 1) water, 50 deg C, 50 deg C, 20 min; 2) water, room temperature View Scheme

1: glacial acetic acid / ethanol / Heating 2: 1.) potassium hydroxide / 1) water, 50 deg C, 50 deg C, 20 min; 2) water, room temperature View Scheme

1: 65 percent / copper (powder), copper(II) chloride dihydrate / H2O / 1) 75 - 80 deg C, 30 min; 2) reflux, 5 h 2: sodium carbonate / toluene; H2O / 19 h / Ambient temperature 3: 1.) sodium hydride / 1) toluene, 70 - 75 deg C, 1 h; 2) toluene, 1 h, 30 deg C 4: 79.5 percent / piperidine, acetic acid / 2 h / Heating View Scheme

1: sodium carbonate / toluene; H2O / 19 h / Ambient temperature 2: 1.) sodium hydride / 1) toluene, 70 - 75 deg C, 1 h; 2) toluene, 1 h, 30 deg C 3: 79.5 percent / piperidine, acetic acid / 2 h / Heating View Scheme

1: 1.) sodium hydride / 1) toluene, 70 - 75 deg C, 1 h; 2) toluene, 1 h, 30 deg C 2: 79.5 percent / piperidine, acetic acid / 2 h / Heating View Scheme