Reacción #687304

Ecuación de reacción

sodium cyanotrihydroborate

hydrochloric acid

hydrochloric acid

1,3-diaminopropan-2-ol

2-pyridine aldehyde

→

aimed product

N,N,N′-tri(2-pyridylmethyl)-1,3-diaminopropan-2-ol

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.ADDITIONAfter the completion of the addition, reaction
3. 3
   Concentraciónthe solution was concentrated to a proper extent
4. 4
   workup.ADDITIONa 0.1 N aqueous sodium hydroxide solution was added
5. 5
   Extracciónthe solution was extracted
6. 6
   OtroThe obtained chloroform phases were collected
7. 7
   Otrodried
8. 8
   Concentraciónconcentrated

Procedimiento

After concentrated hydrochloric acid (60 mL) was added to a solution of 1,3-diaminopropan-2-ol (32.6 g, 362 mmol) in methanol (2400 mL) and further 2-pyridine aldehyde (116.3 g, 1.09 mmol) was added dropwise, sodium cyanotrihydroborate (50.16 g, 798 mmol) was added. After the completion of the addition, reaction was carried out at room temperature for 3 days. After concentrated hydrochloric acid was added to the reaction solution to adjust pH to 6, the solution was concentrated to a proper extent and a 0.1 N aqueous sodium hydroxide solution was added to adjust pH to 7 and the solution was extracted using chloroform. The obtained chloroform phases were collected and dried and thereafter concentrated. The obtained residue was refined by silica gel column chromatography to obtain 34 g of an aimed product.

Fuente