Trifluoroacetic acid → HCID 18797366, compound

HRID 1003575Notes

Reaction equation

HRID 1003575 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[C:7]([C:10]3(O)[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]3)[C:6]=2[CH:24]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[C:7]([C:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH:11]=3)[C:6]=2[CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21268335HCID 21268335, compound

Product 1

HCID 18797366HCID 18797366, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.32 gm (0.86 mMol) 5-chloro-3-(4-hydroxy-1-(tert-butoxycarbonyl)piperidin-4-yl)benzothiophene in 3.0 mL dichloromethane were added 2.0 mL trifluoroacetic acid. The reaction mixture was stirred for 4 hours at room temperature and was then concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, eluting with chloroform containing 5% methanol. Fractions shown to contain product were combined and then concentrated under reduced pressure to give 0.14 gm (64%) of 5-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)benzothiophene as a foam. This material was dissolved in diethyl ether and the solution was saturated with hydrogen chloride. The resulting solution was concentrated under reduced pressure to give the title compound as an orange solid.

Workup

  1. concentrationwas then concentrated under reduced pressure
  2. washeluting with chloroform containing 5% methanol
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-38dc96a5570946e9a8c0f646ca7c36d7
Source dataset
uspto-grants-2000_04
Patent number
US06046215

Reaction notes

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