Hydrochloric Acid → Zantac

HRID 2293632Notes

Reaction equation

HRID 2293632 reaction equation
[CH3:1][NH:2][C:3]([NH:8][CH2:9][CH2:10][S:11][CH2:12][C:13]1[O:17][C:16]([CH2:18][N:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=1)=[CH:4][N+:5]([O-:7])=[O:6].[ClH:22]>N1C=CC=CC=1>[CH3:1][NH:2][C:3]([NH:8][CH2:9][CH2:10][S:11][CH2:12][C:13]1[O:17][C:16]([CH2:18][N:19]([CH3:20])[CH3:21])=[CH:15][CH:14]=1)=[CH:4][N+:5]([O-:7])=[O:6].[ClH:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 5039Ranisen

Product 1

HCID 47909Zantac

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ranitidine free base (6 g) was dissolved in industrial methylated spirits 74° o.p. (42 ml) at ambient temperature (about 20° C.). One equivalent (about 1.6 ml) concentrated HCl was added to the solution. The temperature rose to about 27° C. and 0.3 g pyridine was added to the reaction mixture. The solution was seeded to induce crystallization. The product crystallized to give a thick slurry at 25°-27° C. After 0.5 hour the slurry was cooled to 10°-12° C. for 0.5 hour. The product was filtered off, washed with industrial methylated spirits (5 ml) and dried at 50° C. under reduced pressure to give 5.4 g Form II ranitidine hydrochloride having a melting point of 139°-140° C.

Workup

  1. customat ambient temperature
  2. custom(about 20° C.)
  3. customrose to about 27° C.
  4. customcrystallization
  5. customThe product crystallized
  6. customto give a thick slurry at 25°-27° C
  7. temperatureAfter 0.5 hour the slurry was cooled to 10°-12° C. for 0.5 hour
  8. filtrationThe product was filtered off
  9. washwashed with industrial methylated spirits (5 ml)
  10. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-9e2a63a723c3450d8159eba30d87bf91
Source dataset
uspto-grants-1997_11
Patent number
US05686588

Reaction notes

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