1: n-dipropylamine / 16 h / 15 - 55 °C 2: hydrogen bromide / water / 72 h / 100 °C View Scheme

1: hydrogen 2: method of Krapcho View Scheme

in hexane; toluene T=-40°C; Hydrogenation; 15 h; Title compound not separated from byproducts;

hydrogen Catalytic hydrogenation;

1.1: n-dipropylamine / 16 h / 15 - 55 °C 2.1: hydrogen bromide / water / 72 h / 100 °C 3.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere 4.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C 4.2: pH 2 5.1: acetone / water / 80 °C 6.1: ammonia / water / 5 h / 80 °C 6.2: 0 °C / pH 1 7.1: potassium hydroxide / water / 30 h / 0 °C 7.2: 1.17 h / 0 - 80 °C 7.3: 0.5 h / 80 - 90 °C View Scheme

1.1: n-dipropylamine / 16 h / 15 - 55 °C 2.1: hydrogen bromide / water / 72 h / 100 °C 3.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere 4.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C 4.2: pH 2 5.1: acetone / water / 80 °C 6.1: ammonia / water / 5 h / 80 °C 6.2: 0 °C / pH 1 7.1: potassium hydroxide / water / 30 h / 0 °C 7.2: 1.17 h / 0 - 80 °C 7.3: 0.5 h / 80 - 90 °C View Scheme

1: n-dipropylamine / 16 h / 15 - 55 °C 2: hydrogen bromide / water / 72 h / 100 °C 3: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere View Scheme

1.1: n-dipropylamine / 16 h / 15 - 55 °C 2.1: hydrogen bromide / water / 72 h / 100 °C 3.1: acetyl chloride / 3.08 h / 20 - 55 °C / Inert atmosphere 4.1: ammonia / water; tert-butyl methyl ether / 0 - 20 °C 4.2: pH 2 5.1: acetone / water / 80 °C 6.1: ammonia / water / 5 h / 80 °C 6.2: 0 °C / pH 1 7.1: potassium hydroxide / water / 30 h / 0 °C 7.2: 1.17 h / 0 - 80 °C 7.3: 0.5 h / 80 - 90 °C View Scheme

piperidine; acetic acid in toluene Reflux;