Hydrochloric Acid → N-[2-(4-trifluoromethylphenyl)-ethyl]-glucamine

HRID 352654Notes

Reaction equation

HRID 352654 reaction equation
O=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4].[F:13][C:14]([F:25])([F:24])[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][NH2:23])=[CH:17][CH:16]=1.Cl.[H][H]>[Pd].C(O)C>[F:13][C:14]([F:24])([F:25])[C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][NH:23][CH2:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal2×HCID 19881062-[4-(Trifluoromethyl)phenyl]ethan-1-amineHCID 178418361HCID 178418361, compound3×

Product 1

HCID 9950420N-[2-(4-trifluoromethylphenyl)-ethyl]-glucamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethanol (40 ml) is added to a pressure shaker bomb. One part of glucose is dissolved in the solvent followed by one part of 2-(4-trifluoromethylphenyl)-ethylamine. Hydrochloric acid is added to a pH of about 8 to 9. Wet 50% palladium on carbon 0.1 of a part of glucose is added and the mixture is agitated at about 40 degrees centigrade under about 3 atm of hydrogen gas until hydrogen uptake ceases. The hydrogen is vented and the catalyst is removed by filtration and the filtrated is washed with ethanol and the washings are added to the filtrate. The pH of the solution is lowered to about pH=4 with additional hydrochloric acid and the solvents removed on a rotary evaporator under reduced pressure.

Workup

  1. customthe catalyst is removed by filtration
  2. washthe filtrated is washed with ethanol
  3. additionthe washings are added to the filtrate
  4. customthe solvents removed on a rotary evaporator under reduced pressure

Sources & evidence

ORD record
ord-a2ea6b459da6440e9cef1640ac3fb65d
Source dataset
uspto-grants-2004_06
Patent number
US06747149B2

Reaction notes

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