Sodium Chloride → 1,2,3,6-Tetrahydro-1-(triphenylmethyl)pyridine

HRID 1171748Notes

Reaction equation

HRID 1171748 reaction equation
COC1C=CC(CN2C=C(/C=[C:14]3\[CH2:15][N:16]([C:21]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:17][CH2:18][CH:19]\3O)N=N2)=CC=1.C(O)(=S)C.C(OC(OCC(C)(C)C)N(C)C)C(C)(C)C.[Cl-].[Na+].C(SC1CCN(C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C/C/1=C\C1N=NN(CC2C=CC(OC)=CC=2)C=1)(=O)C>C1(C)C=CC=CC=1>[C:22]1([C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:16]2[CH2:15][CH:14]=[CH:19][CH2:18][CH2:17]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 786231,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamineHCID 68766248HCID 68766248, compoundHCID 86609484HCID 86609484, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 1868871,2,3,6-Tetrahydro-1-(triphenylmethyl)pyridineYield 170.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (E)-3-{[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]methylidene}-1-(triphenylmethyl)piperidin-4-ol (17.45 g) in toluene (300 ml) were added thioacetic acid (4.6 ml) and N,N-dimethylformamide dineopentylacetal (18 ml). The resulting solution was stirred at room temperature for 15 minutes, and the reaction was stopped by an addition of a saturated aqueous sodium chloride solution. The products were extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel using a mixture of hexane, ethyl acetate and dichloromethane (1:1:1) as the eluent to afford an approximately 1:3 mixture of (E)-4-(acetylsulfanyl)-3-{[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]methylidene}-1-(triphenylmethyl)piperidine and 5-(acetylsulfanyl){[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]methylidene}methyl)-1-(triphenylmethyl)-1,2,3,6-tetrahydropyridine (17.83 g, yield: 92%).

Workup

  1. extractionThe products were extracted with ethyl acetate
  2. dry with materialthe extract was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel using
  5. additiona mixture of hexane, ethyl acetate and dichloromethane (1:1:1) as the eluent
  6. customto afford

Sources & evidence

ORD record
ord-ebcee231a52c4573ae858beb04532901
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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