2-Chlorobenzylamine → N-((2-chlorophenyl)methyl)thiophene-2-ethylamine hydrochloride

HRID 1165070Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7]O.C1(C)C=CC(S(OCCC2SC=CC=2)(=O)=O)=CC=1.[Cl:27][C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[CH2:30][NH2:31]>>[ClH:27].[Cl:27][C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[CH2:30][NH:31][CH2:7][CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 666482-Chlorobenzylamine

HCID 794002-Thiopheneethanol

HCID 36820342-Thiopheneethanol tosylate

Product 1

HCID 6454011N-((2-chlorophenyl)methyl)thiophene-2-ethylamine hydrochloride

Procedure

Another synthetic route involved preparation of a 2-(2-thienyl)ethanol, its conversion to 2-(2-thienyl)ethyl paratoluene sulfonate and benzylation with o-chlorobenzylamine to give N-(2-chloro-benzyl)-2-(2-thienyl)ethylamine hydrochloride, which is cyclized to give ticlopidine free base, as described by Braye in U.S. Pat. No. 4,127,580.

Sources & evidence

ORD record: ord-9821706cd9774fa6b5013d08f0448b02
Source dataset: uspto-grants-1990_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04906756

Reaction notes

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