Ranisen → Zantac

HRID 2293629Notes

Reaction equation

HRID 2293629 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

3

Reactant 2

HCID 5039RanisenHCID 10176127Pyridinium chloride

Product 1

HCID 47909Zantac

Procedure

Ranitidine (6 g) was dissolved in industrial methylated spirits 74° o.p. (42 ml) at ambient temperature (about 20° C.). 2.6 g of pyridine hydrochloride was added to the solution. The temperature of the solution rose to 27° C. and the mixture was seeded to induce crystallization. The product crystallized to give a thick slurry at about 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 about 139°-140° C.

Workup

  1. customat ambient temperature
  2. custom(about 20° C.)
  3. customrose to 27° C.
  4. customcrystallization
  5. customThe product crystallized
  6. customto give a thick slurry at about 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-e4438e44a8dd4568813603fbf584456d
Source dataset
uspto-grants-1997_11
Patent number
US05686588

Reaction notes

Loading…