Hydrochloric Acid → 4,5,6,7-Tetrahydrothieno(3,2-c)pyridine

HRID 1638148Notes

Reaction equation

HRID 1638148 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][NH2:8].[N+]([CH:12]=CC1SC=CC=1)([O-])=O.C=O.Cl>>[S:1]1[C:2]2[CH2:6][CH2:7][NH:8][CH2:12][C:3]=2[CH:4]=[CH:5]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 955862-(2-Nitro-vinyl)-thiopheneHCID 116521Thiopheneethanamine

Product 1

HCID 30850764,5,6,7-Tetrahydrothieno(3,2-c)pyridine

Procedure

U.S. Pat. No. 4,906,756 to Lodewijk et al. proposes the reaction of 2-(2-thienyl)ethylamine, prepared from 2-(2-nitrovinyl)thiophene, with formaldehyde to produce the formimine, cyclizing the formimine with hydrochloric acid to produce 4,5,6,7-tetrahydrothieno[3,2,c]pyridine, and converting this compound to ticlopidine free base by reaction with o-chlorobenzylchloride. The free base is then converted to ticlopidine hydrochloride.

Workup

  1. customto produce the formimine

Sources & evidence

ORD record
ord-5c8447b7790448049521bdaef751ba98
Source dataset
uspto-grants-2000_03
Patent number
US06043368

Reaction notes

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