Trifluoroacetic acid → HCID 21268229, compound

HRID 1779626Notes

Reaction equation

HRID 1779626 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([C:10]3(O)[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]3)[S:7][C:6]=2[CH:24]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([C:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH:11]=3)[S:7][C:6]=2[CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21866069HCID 21866069, compound

Product 1

HCID 21268229HCID 21268229, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

A solution of 6-chloro-2-(4-hydroxy-N-t-butoxycarbonylpiperidin-4-yl)benzo[b]thiophene (1.04 g, 2.83 mmol) in methylene chloride (30.0 ml) was treated with 4.36 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, CHCl3 /MeOH 95:5) to give 0.640 g (90%) 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, CHCl3 /MeOH 95:5)

Sources & evidence

ORD record
ord-19abfe9a56f041d8a869e5432a965f1f
Source dataset
uspto-grants-1997_05
Patent number
US05627196

Reaction notes

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