Benzaldehyde → HCID 11148442, compound

A solution of benzaldehyde (1.0 ml, 10.0 mmol) in THF (50 ml) was added with heating at reflux to a solution of 1,6-diaminohexane (5.81 g, 50.0 mmol) and p-toluene sulfonic acid (9.5 1 g, 50.0 mmol) in ethanol (50 ml) and then it was heated to reflux for 3 h under a nitrogen atmosphere. After cooling to room temperature, sodium borohydride (1.13 g, 30.0 mmol) was added to the solution and it was stirred at room temperature for 1 h. The solvent was removed under reduced pressure and the residue dissolved in chloroform. The chloroform phase was washed with water, and dried over magnesium sulphate, the solvent was removed under reduced pressure. The residue was washed with water (25 ml), and it dissolved in chloroform and washed again with water (2×50 ml). Then dried over magnesium sulphate, and the solvent removed under reduced pressure to yield a yellow oil (1.61 g, 78%).

1. temperaturewith heating
2. temperatureit was heated
3. temperatureto reflux for 3 h under a nitrogen atmosphere
4. customThe solvent was removed under reduced pressure
5. dissolutionthe residue dissolved in chloroform
6. washThe chloroform phase was washed with water
7. dry with materialdried over magnesium sulphate
8. customthe solvent was removed under reduced pressure
9. washThe residue was washed with water (25 ml), and it
10. dissolutiondissolved in chloroform
11. washwashed again with water (2×50 ml)
12. dry with materialThen dried over magnesium sulphate
13. customthe solvent removed under reduced pressure

ORD record

ord-34abb62f7a7d433b8a348c1e2c49dd5d

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06664407B2