Hydrochloric Acid → Zantac

HRID 1376926Notes

Reaction equation

HRID 1376926 reaction equation
[ClH:1].[CH3:2][NH:3][C:4]([NH:9][CH2:10][CH2:11][S:12][CH2:13][C:14]1[O:18][C:17]([CH2:19][N:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=1)=[CH:5][N+:6]([O-:8])=[O:7]>O>[CH3:2][NH:3][C:4]([NH:9][CH2:10][CH2:11][S:12][CH2:13][C:14]1[O:18][C:17]([CH2:19][N:20]([CH3:21])[CH3:22])=[CH:16][CH:15]=1)=[CH:5][N+:6]([O-:8])=[O:7].[ClH:1]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 5039Ranisen2×

Product 1

HCID 47909Zantac

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The seeding material of pure Form 1 ranitidine hydrochloride may be prepared by dissolving ranitidine in a solvent, preferably methylene chloride, at room temperature (20° to 25° C.), wherein the ratio of ranitidine to methylene chloride is from about 1:1 to 1:5, preferably 1:4, and treating the solution thus obtained with aqueous concentrated hydrochloric acid (e. g., 35 to 38% w/w). The hydrochloric acid and ranitidine may be mixed without cooling to form a reaction mixture. Preferably, however, the hydrochloric acid and ranitidine are mixed with cooling at -5° C. to 10° C. The reaction mixture is then heated under reflux and during heating, water is stripped off under azeotropic conditions. Preferably, the reaction mixture is heated under reflux for at least 4 hours, more preferably for approximately 6.5 hours. Alternatively, the reaction may be carried out under mild reaction conditions, such as, for example from 0° to 10° C. up to 20° to 25° C. for approximately 6.5 hours. The Form 1 ranitidine hydrochloride crystals that are formed are then filtered off from the crystallization medium, washed with ethanol and dried.

Workup

  1. temperaturewithout cooling
  2. customto form a reaction mixture
  3. temperaturewith cooling at -5° C. to 10° C
  4. temperatureThe reaction mixture is then heated
  5. temperatureunder reflux
  6. temperatureduring heating
  7. temperaturePreferably, the reaction mixture is heated
  8. temperatureunder reflux for at least 4 hours, more preferably for approximately 6.5 hours
  9. customAlternatively, the reaction
  10. custommay be carried out under mild reaction conditions

Sources & evidence

ORD record
ord-3a22675c34ce4c00856cd4ca45cdc04c
Source dataset
uspto-grants-1997_09
Patent number
US05663381

Reaction notes

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