Yield: 92%

Reaction Conditions:

with hydrogenchloride;water in 1,4-dioxane at 20; for 16 h;

Steps:

3.B
Step B: To a magnetically stirred solution of N'-butylhydrazine-carboxylic acid tert-butyl ester (intermediate XIII-1) (13.17 gram, 70 mmol) in 1,4-dioxane (100 ml) was added excess (12 mol equivalents) hydrochloric acid (12 N) and the resulting mixture was reacted for 16 hours at room temperature. The resulting mixture was concentrated in vacuo and triturated with diethyl ether to give n-butylhydrazine.HCl.H₂O (Intermediate XI-2) (9.63 gram, 92% yield). ¹H-NMR (400 MHz, DMSO-d₆/CDCl₃=4/1 (v/v)) δ 0.93 (t, J=7, 3H), 1.32-1.43 (m, 2H), 1.56-1.65 (m, 2H), 2.92-2.98 (m, 2H), 7.20 (br s, 6H).

References:

Solvay Pharmaceuticals B.V. US2009/82396, 2009, A1 Location in patent:Page/Page column 13