1,3-Dioxolane → Ticlopidine Hydrochloride

HRID 1638149Notes

Reaction equation

HRID 1638149 reaction equation
[ClH:1].[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][NH:10][CH2:11][CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1.O1CCO[CH2:19]1>>[CH:6]1[CH:7]=[CH:8][C:3]([Cl:2])=[C:4]([CH2:9][N:10]2[CH2:19][C:17]3[CH:16]=[CH:15][S:14][C:13]=3[CH2:12][CH2:11]2)[CH:5]=1.[ClH:1]

Participants

3

Reactant 2

HCID 125861,3-DioxolaneHCID 6454011N-((2-chlorophenyl)methyl)thiophene-2-ethylamine hydrochloride

Product 1

HCID 65335Ticlopidine HydrochlorideYield 95%

Procedure

N-[(2-chlorophenyl-methyl)]-2-(2-thienyl)ethylamine HCl (28.8 g) is suspended in 75 ml of 1,3-dioxolane. Hydrochloric acid at 37% concentration (0.25 ml) is added and the temperature of the reaction mixture is brought to 80° C. for 5 hours. Thereafter the reaction is complete. The mixture is cooled to room temperature, and the compound precipitates out. To complete the precipitation and simplify filtration, 75 ml of ethyl acetate is added to the reaction mixture. The filter cake is washed with ethyl acetate (2×20 ml) and dried at 60° C. UV. Ticlopidine HCl (28.5 g, 95% yield) is obtained with m.p. 208-210° C.

Workup

  1. concentrationHydrochloric acid at 37% concentration (0.25 ml)
  2. additionis added
  3. customthe compound precipitates out
  4. customthe precipitation
  5. filtrationfiltration, 75 ml of ethyl acetate
  6. additionis added to the reaction mixture
  7. washThe filter cake is washed with ethyl acetate (2×20 ml)
  8. customdried at 60° C

Sources & evidence

ORD record
ord-fbb5209dcd3f4ee5b194c947a9357814
Source dataset
uspto-grants-2000_03
Patent number
US06043368

Reaction notes

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