Hydrochloric Acid → HCID 22869670, compound

A 2.3-L Parr shaker bottle is charged with 1 L of 3A ethanol and 83g (1.1 mol) of n-butylamine. The mixture is stirred and cooled while 16 mL of 12N hydrochloric acid is slowly added. The pH after this addition is 10. To the 2.3-L Parr bottle is added 200 g (1.1 mol) of D-glucose followed by 60 g of 4% palladium-on-carbon (50% water-wet). The mixture is agitated rapidly and hydrogenated at a constant pressure of 4 atm of hydrogen at 60±5° C. until the reaction is complete (as indicated by hydrogen uptake). The hydrogen is vented and the 4% palladium-on-carbon is removed by filtration through a layer of powdered cellulose. The catalyst is washed with 100 mL of 3A ethanol followed by 50 mL of water. The wash is combined with the filtrate to give a solution containing a mixture of N-butyl glucamine and the corresponding hydrochloride salt. The mixture is stirred and cooled while 80 mL of 12N hydrochloric acid is slowly added. The pH after this addition is 2.5. The ethanol is removed by distillation under reduced pressure. The residue contains approximately 270 g of N-n-butyl glucamine hydrochloride. The residue is diluted to 500 mL with water to produce a bulk solution of N-n-butyl glucamine hydrochloride which is used in the next step without purification.

1. additionis slowly added
2. additionThe pH after this addition
3. stirringThe mixture is agitated rapidly
4. customthe 4% palladium-on-carbon is removed by filtration through a layer of powdered cellulose
5. washThe catalyst is washed with 100 mL of 3A ethanol
6. customto give a solution
7. additioncontaining
8. stirringThe mixture is stirred
9. additionis slowly added
10. additionThe pH after this addition
11. customThe ethanol is removed by distillation under reduced pressure
12. additionThe residue is diluted to 500 mL with water

ORD record

ord-d27af4b1b62d4fb6b439555519e01fab

Source dataset

uspto-grants-1999_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05916784