Hydrochloric Acid → Zantac

HRID 2293630Notes

Reaction equation

HRID 2293630 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].N1C=CC=CC=1>CC(O)C>[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 5039Ranisen

Product 1

HCID 47909Zantac

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

One equivalent (about 5.3 ml) of concentrated hydrochloric acid was added to a solution of ranitidine (20 g) in a mixture of propan-2-ol (300 ml) at 45° C. The mixture was heated to 50° C. and then 0.4 g pyridine was added to the reaction mixture. The resulting solution was stirred at 50° C. to allow the product to crystallize. The slurry was cooled to 10°-12° C. and the product was filtered off, washed with propan-2-ol (2×27 ml) and dried at 50° C. under reduced pressure to give 22 g Form II ranitidine hydrochloride having a melting point of 139°-141° C.

Workup

  1. customto crystallize
  2. temperatureThe slurry was cooled to 10°-12° C.
  3. filtrationthe product was filtered off
  4. washwashed with propan-2-ol (2×27 ml)
  5. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-d005bb148dd2456b9677fa2a3fdb2fd8
Source dataset
uspto-grants-1997_11
Patent number
US05686588

Reaction notes

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