Propanal → N,N-dipropylbutane-1,4-diamine

N-(4-aminobutyl)-carbamic acid t-butyl ester (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (500 mg) was dissolved in methanol (10 ml) and then added with propionaldehyde (manufactured by Tokyo Kasei Kogyo Co., Ltd.) (0.418 ml), sodium cyanoborohydride (404 mg), and trimethyl orthoacetate (1.60 g), and the whole was stirred at room temperature for 12 hours. After completion of the reaction, the solvent was distilled off. Then, the resultant was added with chloroform, washed with distilled water and a saturated saline solution, and then dried with anhydrous sodium sulfate. After concentration and evaporation to dryness of the solution, methanol (4.0 ml) and a 4 mol/l hydrogen chloride/dioxane solution (4.0 ml) were added to the dried product and the whole was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off and then dioxane was added to wash the residue, thereby obtaining a hydrochloride (654 mg) of the subject compound.

1. customAfter completion of the reaction
2. distillationthe solvent was distilled off
3. additionThen, the resultant was added with chloroform
4. washwashed with distilled water
5. dry with materiala saturated saline solution, and then dried with anhydrous sodium sulfate
6. concentrationAfter concentration and evaporation to dryness of the solution, methanol (4.0 ml)
7. additiona 4 mol/l hydrogen chloride/dioxane solution (4.0 ml) were added to the dried product
8. stirringthe whole was stirred at room temperature for 2 hours
9. customAfter completion of the reaction
10. distillationthe solvent was distilled off
11. additiondioxane was added
12. washto wash the residue

ORD record

ord-dd73c5f202f4475b917e3e5008ac8457

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932281B2