Hydrochloric Acid → Ticlopidine Hydrochloride

HRID 1638150Notes

Reaction equation

HRID 1638150 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.O1CCCO[CH2:19]1.Cl>C(O)(C)C>[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 104501,3-DioxaneHCID 6454011N-((2-chlorophenyl)methyl)thiophene-2-ethylamine hydrochloride

Product 1

HCID 65335Ticlopidine HydrochlorideYield 82%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

N-[(2-chlorophenyl-methyl)]-2-(2-thienyl)ethylamine HCl (28.8 g) is suspended in 75 ml of iso-propanol. 1,3-Dioxane (13.2 g) and 0.25 ml of hydrochloric acid (37% concentration) are added. The reaction mixture is heated to 80° C. for 24 hours. Thereafter, the mixture is cooled to 10° C. and the precipitate is filtered and washed twice with 10 ml of frozen iso-propanol. The product is desiccated at 60° C. UV to yield 24.6 g (82%) Ticlopidine hydrochloride with chemical-physical characteristics as described in Example 1.

Workup

  1. temperatureThereafter, the mixture is cooled to 10° C.
  2. filtrationthe precipitate is filtered
  3. washwashed twice with 10 ml of frozen iso-propanol
  4. customis desiccated at 60° C

Sources & evidence

ORD record
ord-f9afe6551c06405cb4128657cddb614e
Source dataset
uspto-grants-2000_03
Patent number
US06043368

Reaction notes

Loading…