Hydrochloric Acid → 4-(Benzofuran-3-yl)-1,2,3,6-tetrahydropyridine hydrochloride

HRID 1409859Notes

Reaction equation

HRID 1409859 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH:11]=2)=[CH:2]1.[ClH:23]>ClCCl.O1CCOCC1>[ClH:23].[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH:11]=2)=[CH:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 70945173tert-butyl 4-(benzofuran-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 709452624-(Benzofuran-3-yl)-1,2,3,6-tetrahydropyridine hydrochlorideYield 85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of tert-butyl 4-(benzofuran-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (2.06 g, 6.88 mmol) in dichloromethane (50 ml) was added at room temperature hydrochloric acid solution (4M in dioxane, 25.8 ml, 103 mmol) and the reaction mixture was allowed to stir for 2 h. The reaction mixture was diluted with dioxane (25 ml), the precipitate was collected by filtration, washed with dioxane and dried to yield 4-(benzofuran-3-yl)-1,2,3,6-tetrahydropyridine hydrochloride as off-white solid (1.37 g, 85%), MS (ISP) m/z=200.2 [(M+H)−], mp 276° C.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with dioxane
  3. customdried

Sources & evidence

ORD record
ord-48bfedc1d5a94bf0a3280c82aa4901c7
Source dataset
uspto-grants-2014_12
Patent number
US08921397B2

Reaction notes

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