Hydrochloric Acid → Ticlopidine Hydrochloride

HRID 1638151Notes

Reaction equation

HRID 1638151 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.S1CCCS[CH2:19]1.Cl>C(COC)OC>[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 104511,3-DithianeHCID 6454011N-((2-chlorophenyl)methyl)thiophene-2-ethylamine hydrochloride

Product 1

HCID 65335Ticlopidine HydrochlorideYield 62.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
10 °C

Procedure

N-[(2-chlorophenyl-methyl)]-2-(2-thienyl)ethylamine HCl (14.4 g) is suspended into 50 ml of dimethoxyethane. 1,3-Dithiane (9 g) and 0.12 ml of 37% hydrochloride acid are added. The reaction mixture is refluxed for 24 hours. Thereafter, the mixture is cooled to 10° C. and the crystalline precipitate is filtered and washed twice with 5 ml of dimethoxyethane. The product is dried at 60° C. under vacuum to yield 9.4 g (62.7%) of ticlopidine hydrochloride having the same physico-chemical characteristics as reported in Example 1.

Workup

  1. temperatureThe reaction mixture is refluxed for 24 hours
  2. filtrationthe crystalline precipitate is filtered
  3. washwashed twice with 5 ml of dimethoxyethane
  4. customThe product is dried at 60° C. under vacuum

Sources & evidence

ORD record
ord-c52d1873fafa43198faf4acbd16b61be
Source dataset
uspto-grants-2000_03
Patent number
US06043368

Reaction notes

Loading…