Triphenylphosphine → (E)-4-(acetylsulfanyl)-3-benzylidene-1-(triphenylmethyl)piperidine

HRID 1171635Notes

Reaction equation

HRID 1171635 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH:34](=[C:41]1/[CH2:42][N:43]([C:48]([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH2:44][CH2:45][CH:46]/1O)/[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[C:67]([OH:70])(=[S:69])[CH3:68]>O1CCCC1.C1(C)C=CC=CC=1>[C:67]([S:69][CH:46]1[CH2:45][CH2:44][N:43]([C:48]([C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)([C:61]2[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=2)[C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH2:42]/[C:41]/1=[CH:34]\[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:70])[CH3:68]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 68764908(E)-3-Benzylidene-1-(triphenylmethyl)piperidin-4-olHCID 178418634HCID 178418634, compound

Product 1

HCID 86609403(E)-4-(acetylsulfanyl)-3-benzylidene-1-(triphenylmethyl)piperidine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of triphenylphosphine (6.39 g) in tetrahydrofuran (100 ml) was added a solution of diisopropyl azodicarboxylate in toluene (13.11 ml) under ice-cooling, and the resulting mixture was stirred at the same temperature for 1 hour. Subsequently, to the reaction mixture was added dropwise a solution of (E)-3-benzylidene-1-(triphenylmethyl)piperidin-4-ol (5.26 g) and thioacetic acid (1.74 ml) in tetrahydrofuran (50 ml) at the same temperature, and the resulting mixture was furthermore stirred at room temperature for 2.5 hours. The reaction mixture was evaporated in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (2:23) as the eluent to afford (E)-4-(acetylsulfanyl)-3-benzylidene-1-(triphenylmethyl)piperidine (containing impurities) as a pale yellow amorphous solid.

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was furthermore stirred at room temperature for 2.5 hours
  3. customThe reaction mixture was evaporated in vacuo
  4. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-6c7f929e5e734f368df5d6aa0d63abaa
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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