Potassium Carbonate → 2-Nitro-4-((1-tert-butyloxycarbonylpiperidin-4-yl)methoxy)-5-methoxybenzonitrile

HRID 896251Notes

Reaction equation

HRID 896251 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([OH:12])[C:9]([O:13][CH3:14])=[CH:8][C:5]=1[C:6]#[N:7])([O-:3])=[O:2].C1(C)C=CC(S(O[CH2:25][CH:26]2[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]2)(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(#N)C.O>[N+:1]([C:4]1[CH:11]=[C:10]([O:12][CH2:25][CH:26]2[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:33])[CH2:28][CH2:27]2)[C:9]([O:13][CH3:14])=[CH:8][C:5]=1[C:6]#[N:7])([O-:3])=[O:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 106428511-(tert-Butoxycarbonyl)-4-((p-toluenesulfonyloxy)methyl)piperidineHCID 22349623HCID 22349623, compound

Product 1

HCID 223496402-Nitro-4-((1-tert-butyloxycarbonylpiperidin-4-yl)methoxy)-5-methoxybenzonitrileYield 80.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

2-nitro-4-hydroxy-5-methoxybenzonitrile (388 mg, 2 mmol) in DMF (5 ml) and acetonitrile (5 ml) was reacted with 4-(4-tolylsulphonyloxymethyl)-1-tert-butyloxycarbonyl-piperidine (738 mg, 2 mmol) and K2CO3 (414 mg, 3 mmol) at 110° C. for 3.5 hours. The mixture was diluted with water, extracted with ethylacetate, washed HCl (2N), dried over MgSO4, evaporated to give title compound (630 mg, 80%).

Workup

  1. extractionextracted with ethylacetate
  2. washwashed HCl (2N)
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-b1cd37ebac2e40398f8c6486ba339e42
Source dataset
uspto-grants-2005_07
Patent number
US06919338B2

Reaction notes

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