Ranisen → Zantac

HRID 2293628Notes

Reaction equation

HRID 2293628 reaction equation
[ClH:1].N1C=CC=CC=1.[CH3:8][NH:9][C:10]([NH:15][CH2:16][CH2:17][S:18][CH2:19][C:20]1[O:24][C:23]([CH2:25][N:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=1)=[CH:11][N+:12]([O-:14])=[O:13]>CC(O)(C)C>[CH3:8][NH:9][C:10]([NH:15][CH2:16][CH2:17][S:18][CH2:19][C:20]1[O:24][C:23]([CH2:25][N:26]([CH3:27])[CH3:28])=[CH:22][CH:21]=1)=[CH:11][N+:12]([O-:14])=[O:13].[ClH:1]

Participants

4

Reactant 2

HCID 5039RanisenHCID 10176127Pyridinium chloride

Product 1

HCID 47909ZantacYield 89%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
40 °C

Procedure

Pyridine hydrochloride (2.6 g) was added to a solution of ranitidine (6 g) in 2-methylpropan-2-ol. The mixture was stirred at 40° C. to allow the product to crystallize and the resulting slurry was cooled to 20° C. The product was filtered off, washed with 2-methylpropan-2-ol and dried at 50° C. under reduced pressure to give Form II ranitidine hydrochloride (5.96 g) having a melting point of about 141°-142° C.

Workup

  1. customto crystallize
  2. temperaturethe resulting slurry was cooled to 20° C
  3. filtrationThe product was filtered off
  4. washwashed with 2-methylpropan-2-ol
  5. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-66c3f16489eb44ebb0d11fdd2d21e432
Source dataset
uspto-grants-1997_11
Patent number
US05686588

Reaction notes

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