Hydrochloric Acid → Isopilocarpic Acid Sodium Salt

HRID 1648495Notes

Reaction equation

HRID 1648495 reaction equation
[CH3:1][CH2:2][C@@H:3]1[C:7](=[O:8])[O:6][CH2:5][C@@H:4]1[CH2:9][C:10]1[N:14]([CH3:15])[CH:13]=[N:12][CH:11]=1.Cl.[OH-:17].[Na+:18].Cl>O>[CH3:1][CH2:2][C@@H:3]([C:7]([O-:6])=[O:8])[C@H:4]([CH2:5][OH:17])[CH2:9][C:10]1[N:14]([CH3:15])[CH:13]=[N:12][CH:11]=1.[Na+:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5909Pilocarpine HydrochlorideHCID 14798Sodium Hydroxide

Product 1

HCID 71749484Isopilocarpic Acid Sodium Salt

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Pilocarpine hydrochloride (3.92 g; 16.00 moles) was dissolved in distilled water (4 ml) and the solution was cooled to about 0° C. To the solution 18 ml of ice cold 2M NaOH were added in four portions. The solution was left standing at about 0° C. for one hour. After neutralizing excess NaOH with 5 ml of 1M HCl, the solution was evaporated under reduced pressure. The residue was dissolved in 60 ml of absolute ethanol and mixed for 10 minutes at 60° C. After cooling to 4° C. undissolved NaCl was removed by filtration. The filtrate was evaporated under reduced pressure, whereby 3.93 g of sodium pilocarpate were obtained as a white, extremely hygroscopic substance.

Workup

  1. waitThe solution was left
  2. customthe solution was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in 60 ml of absolute ethanol
  4. additionmixed for 10 minutes at 60° C
  5. temperatureAfter cooling to 4° C. undissolved NaCl
  6. customwas removed by filtration
  7. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d37ed0d5c9d84a7dab62e0522dee2f7f
Source dataset
uspto-grants-1995_07
Patent number
US05436350

Reaction notes

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