Trifluoroacetic acid → HCID 22494778, compound

HRID 1816711Notes

Reaction equation

HRID 1816711 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][CH:10]1[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][CH:10]1[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 22494630HCID 22494630, compound

Product 1

HCID 22494778HCID 22494778, compoundYield 205.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(6-methoxyhexylthio)-N-t-butoxycarbonylpiperidine (3.32 g) in dichloromethane (40 ml) were added triethylsilane (8.0 ml) and trifluoroacetic acid (15.4 ml) with stirring in an ice bath. The mixture was stirred at ambient temperature for 2 hours. The reaction mixture was evaporated in vacuo. The resulting residue was chromatographed on silica gel (400 ml) eluting with a mixture of dichloromethane and methanol (4:1 v/v). The fractions containing the object compound were collected and evaporated under reduced pressure to give 4-(6-methoxyhexylthio)piperidine (4.77 g). This compound was immediately used as the starting compound for the next step.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 2 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. customThe resulting residue was chromatographed on silica gel (400 ml)
  4. washeluting with a mixture of dichloromethane and methanol (4:1 v/v)
  5. additionThe fractions containing the object compound
  6. customwere collected
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3658631cfbc74ba89dad0a8ac12c6635
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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