Hydrochloric Acid → Ticlopidine Hydrochloride

HRID 1165073Notes

Reaction equation

HRID 1165073 reaction equation
[ClH:1].C(O)(C)C.[CH:6]1[CH:7]=[CH:8][C:9]([Cl:22])=[C:10]([CH2:12][N:13]2[CH2:21][C:17]3[CH:18]=[CH:19][S:20][C:16]=3[CH2:15][CH2:14]2)[CH:11]=1>C1(C)C=CC=CC=1>[CH:6]1[CH:7]=[CH:8][C:9]([Cl:22])=[C:10]([CH2:12][N:13]2[CH2:21][C:17]3[CH:18]=[CH:19][S:20][C:16]=3[CH2:15][CH2:14]2)[CH:11]=1.[ClH:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 5472Ticlopidine

Product 1

HCID 65335Ticlopidine Hydrochloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Gaseous HCl (0.22 g, 0.006 mole) is bubbled into 50 ml isopropanol. The resulting solution is added dropwise to ticlopidine free base (1.5 g, 0.005 mole) in 50 ml toluene, prepared, for example as described in Example 3C, maintaining the temperature below 40° C. during the addition. The reaction mixture is stirred for 1 hour, cooled to about 5°-10° C. for 1 hour, and the precipitate separated by centrifugation. An acetone slurry is made of the precipitate, brought to reflux for 1 hour, and cooled to about 5°-10° C. for 1 hour. The precipitate, ticlopidine hydrochloride (Formula III), is separated by centrifugation, dried at 65°-70° C. under vacuum, and recrystallized from methanol. (m.p. 206.5°-207.5° C.)

Workup

  1. temperaturemaintaining the temperature below 40° C.
  2. additionduring the addition
  3. temperaturecooled to about 5°-10° C. for 1 hour
  4. customthe precipitate separated by centrifugation
  5. temperatureto reflux for 1 hour
  6. temperaturecooled to about 5°-10° C. for 1 hour
  7. customThe precipitate, ticlopidine hydrochloride (Formula III), is separated by centrifugation
  8. customdried at 65°-70° C. under vacuum
  9. customrecrystallized from methanol

Sources & evidence

ORD record
ord-a7347cccfcda4ec1b9581253c33f6818
Source dataset
uspto-grants-1990_03
Patent number
US04906756

Reaction notes

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