Trifluoroacetic acid → HCID 21268220, compound

HRID 1900980Notes

Reaction equation

HRID 1900980 reaction equation
[Cl:1][C:2]1[C:10]2[CH:9]=[C:8]([C:11]3(O)[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]3)[S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[C:10]2[CH:9]=[C:8]([C:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH:12]=3)[S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21268219HCID 21268219, compound

Product 1

HCID 21268220HCID 21268220, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

A solution of 4-chloro-2-(4-hydroxy-N-t-butoxycarbonylpiperidin-4-yl)benzo[b]thiophene (0.290 g, 0.79 mmol) in methylene chloride (4.0 ml) was treated with 1.5 ml of trifluoroacetic acid and stirred at 23° C. for 4 hours. The reaction was concentrated to a foam under reduced pressure and the residue chromatographed (silica gel, chloroform/methanol 95:5) to give 0.175 g (88%) of a tan powder. FDMS m/e=250 (M+ of free base)

Workup

  1. concentrationThe reaction was concentrated to a foam under reduced pressure
  2. customthe residue chromatographed (silica gel, chloroform/methanol 95:5)

Sources & evidence

ORD record
ord-2f88831999dc4098a3b5ef3c76a2eb6a
Source dataset
uspto-grants-1996_11
Patent number
US05576321

Reaction notes

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