Triethylamine → HCID 67337882, compound

HRID 1921185Notes

Reaction equation

HRID 1921185 reaction equation
Cl.C([N:5]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:7]2([CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6]1)(=O)C.FC(F)(F)S(O[CH2:25][C:26]([F:29])([F:28])[F:27])(=O)=O.C(N(CC)CC)C>CC(C)=O>[F:27][C:26]([F:29])([F:28])[CH2:25][N:10]1[CH2:9][CH2:8][C:7]2([C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:5][CH2:6]2)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 217029641-(Spiro[indole-3,4'-piperidin]-1(2H)-yl)ethan-1-one--hydrogen chloride (1/1)

Product 1

HCID 67337882HCID 67337882, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-acetyl-1,2-dihydrospiro[indole-3,4′-piperidine] hydrochloride, [Chen et al. Tetrahedron Lett. 1996, 37(30), 5233-5234] (200 mg, 0.750 mmol), 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.128 mL, 0.900 mmol), and triethylamine (0.522 mL, 3.75 mmol) in acetone (2 mL) was heated at reflux for 15 h. The mixture was allowed to cool, and the solvent removed under reduced pressure. The residue was taken up in CH2Cl2 (10 mL) and washed with saturated aqueous NaHCO3 (10 mL). The aqueous layer was further extracted with CH2Cl2 (2×10 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 50:50, to provide the title compound. MS: m/z=271 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 15 h
  3. temperatureto cool
  4. customthe solvent removed under reduced pressure
  5. washwashed with saturated aqueous NaHCO3 (10 mL)
  6. extractionThe aqueous layer was further extracted with CH2Cl2 (2×10 mL)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by silica gel chromatography
  11. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-073013142d5e4ed8a875b0cfd4c96f91
Source dataset
uspto-grants-2012_05
Patent number
US08173655B2

Reaction notes

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