Hydrochloric Acid → Ticlopidine Hydrochloride

HRID 46678

Reaction equation

HRID 46678 reaction equation
C=O.[CH3:3]S(O)(=O)=O.[Cl:8][C:9]1[CH:23]=[CH:22][CH:21]=[CH:20][C:10]=1[CH2:11][NH:12][CH2:13][CH2:14][C:15]1[S:16][CH:17]=[CH:18][CH:19]=1.[OH-].[Na+].Cl>CN(C)C=O.C(O)C>[ClH:8].[Cl:8][C:9]1[CH:23]=[CH:22][CH:21]=[CH:20][C:10]=1[CH2:11][N:12]1[CH2:13][CH2:14][C:15]2[S:16][CH:17]=[CH:18][C:19]=2[CH2:3]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 6454012N-((2-chlorophenyl)methyl)thiophene-3-ethylamine

Product 1

HCID 65335Ticlopidine HydrochlorideYield 146.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
20 °C

Procedure

To 2.25 g (0.075 M) paraformaldehyde suspended in 20 ml dimethylformamide are added 9.61 g (0.1 M) methanesulfonic acid. The medium being at a temperature of 72° C., 13 g (0.05 M) N-(2-chloro-benzyl)-2-(2-thienyl)ethylamine dissolved in 5 ml dimethylformamide are added over 2 minutes. The temperature of the reaction medium reaches 90° C. The reaction medium is then cooled to 20° C. and poured over 50 ml 4N sodium hydroxide. The material is extracted with 1×30 ml and then 1×20 ml methylene chloride. The organic phases are combined, dried over sodium sulfate and evaporated, to give an oil which is taken up into 30 ml ethanol in which are dissolved 0.15 mole gaseous hydrochloric acid. After partial evaporation of the ethanol, the desired product precipitates out. It is filtered, washed with acetone and dried, to give 11.35 g 5-(2-chloro-benzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride (Yield: 75.6%).

Workup

  1. additionare added over 2 minutes
  2. custommedium reaches 90° C
  3. extractionThe material is extracted with 1×30 ml
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto give an oil which
  7. customAfter partial evaporation of the ethanol
  8. customthe desired product precipitates out
  9. filtrationIt is filtered
  10. washwashed with acetone
  11. customdried

Sources & evidence

ORD record
ord-6a087057b35f4230abd8f03b91abb4e0
Source dataset
uspto-grants-1979_11
Patent number
US04174448

Linked notes

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