1,4-Dioxane hydrochloride → 2-[4-(Trifluoromethyl)phenyl]-4,5,6,7-tetrahydro[1,3]thiazolo[4,5-c]pyridine hydrochloride

HRID 1360175Notes

Reaction equation

HRID 1360175 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]3[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][C:12]=3[N:24]=2)=[CH:5][CH:4]=1.[ClH:27].O1CCOCC1>>[ClH:27].[F:26][C:2]([F:1])([F:25])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]3[CH2:16][CH2:15][NH:14][CH2:13][C:12]=3[N:24]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 66969278t-butyl 2-[4-(trifluoromethyl)phenyl]-6,7-dihydro[1,3]thiazolo[4,5-c]pyridin-5(4H)-carboxylate2×

Product 1

HCID 669696262-[4-(Trifluoromethyl)phenyl]-4,5,6,7-tetrahydro[1,3]thiazolo[4,5-c]pyridine hydrochlorideYield 58%

Procedure

0.30 g (0.91 mmol) of t-butyl 2-[4-(trifluoromethyl)phenyl]-6,7-dihydro[1,3]thiazol o[4,5-c]pyridin-5(4H)-carboxylate (product of step 3) was dissolved in 15 mL of 4.0 M HCl/Dioxan solution, followed by stirring for 2 hours. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to give 0.15 g (0.53 mmol) of the title compound in a yield of 58%.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4e3135d86ec8463ebadb0944b91d6205
Source dataset
uspto-grants-2011_02
Patent number
US07879848B2

Reaction notes

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