Hydrochloric Acid → HCID 22869670, compound

HRID 1450128Notes

Reaction equation

HRID 1450128 reaction equation
C(N)CCC.[ClH:6].[H][H].[CH2:9]([NH:13][CH2:14][C@@H:15]([C@H:17]([C@@H:19]([C@@H:21]([CH2:23][OH:24])[OH:22])[OH:20])[OH:18])[OH:16])[CH2:10][CH2:11][CH3:12]>[Pd].C(O)C>[ClH:6].[CH2:9]([NH:13][CH2:14][C@@H:15]([C@H:17]([C@@H:19]([C@@H:21]([CH2:23][OH:24])[OH:22])[OH:20])[OH:18])[OH:16])[CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8007ButylamineHCID 13424553HCID 13424553, compoundHCID 178418361HCID 178418361, compound3×

Product 1

HCID 22869670HCID 22869670, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 2.3-L Parr shaker bottle is charged with 1L 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 200g (1.1 mol) of n-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 arm 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.

Workup

  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

Sources & evidence

ORD record
ord-b92eec69f8df474a9853490988c76825
Source dataset
uspto-grants-1997_02
Patent number
US05602013

Reaction notes

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