Hydrochloric Acid → HCID 77139728, compound

HRID 1040298Notes

Reaction equation

HRID 1040298 reaction equation
[CH3:1][N:2]([CH3:26])[CH2:3][CH:4]([C:6]([C:9]1[CH:10]=[C:11]([O:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)=[CH:7][CH3:8])[CH3:5].Cl>[Pd].C(O)C>[CH3:26][N:2]([CH3:1])[CH2:3][CH:4]([CH3:5])[CH:6]([C:9]1[CH:10]=[C:11]([O:15][S:16]([C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)(=[O:17])=[O:18])[CH:12]=[CH:13][CH:14]=1)[CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 77139727[1RS]-toluene-4-sulfonic acid 3-[1-(2-dimethylamino-1-methyl-ethyl)-propenyl]-phenyl ester

Product 1

HCID 77139728HCID 77139728, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of [1RS]-toluene-4-sulfonic acid 3-[1-(2-dimethylamino-1-methyl-ethyl)-propenyl]-phenyl ester (10 g, 0.03 mol), ethanol (38 ml), concentrated hydrochloric acid (4.5 ml, 30%) and Pd/C (10%, 3 g) was hydrogenated at 5 kg/cm2 for 10 hours. The reaction mixture was filtered through hyflo bed and the filtrate was distilled off to remove ethanol. Water (40 ml) was added to the resulting residue at ambient temperature and reaction mixture was washed with isopropyl ether (2×15 ml). Aqueous sodium carbonate (23 ml, 20%) was added to the reaction mixture till pH 7-8 and saturated with sodium chloride (3.5 g). Resulting product was extracted with dichloromethane (3×50 ml). All organic extracts were combined, washed with brine, dried and solvent distilled off to give 9.8 g of the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through hyflo bed
  2. distillationthe filtrate was distilled off
  3. customto remove ethanol
  4. additionWater (40 ml) was added to the resulting residue at ambient temperature
  5. customreaction mixture
  6. washwas washed with isopropyl ether (2×15 ml)
  7. additionAqueous sodium carbonate (23 ml, 20%) was added to the reaction mixture till pH 7-8 and saturated with sodium chloride (3.5 g)
  8. extractionResulting product was extracted with dichloromethane (3×50 ml)
  9. washwashed with brine
  10. customdried
  11. distillationsolvent distilled off

Sources & evidence

ORD record
ord-56b3aab9b913461185eb14060e6d4efd
Source dataset
uspto-grants-2013_10
Patent number
US08552219B2

Reaction notes

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