Potassium Carbonate → ethyl 1-(4-cyanophenyl)piperidine-4-carboxylate

HRID 734317Notes

Reaction equation

HRID 734317 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH2:10]([O:12][C:13]([CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)=[O:14])[CH3:11].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([N:18]2[CH2:19][CH2:20][CH:15]([C:13]([O:12][CH2:10][CH3:11])=[O:14])[CH2:16][CH2:17]2)=[CH:3][CH:4]=1)#[N:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 2779638ethyl 1-(4-cyanophenyl)piperidine-4-carboxylateYield 91.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To 4-fluorobenzonitrile (11.56 g) in DMSO (200 ml) was added piperidine-4carboxylic acid ethyl ester (15 g) and potassium carbonate (14.4 g) and the reaction was heated to 120° C. for 4 h. After cooling solvent was evaporated and the residue taken up into EtOAc (150 ml) and washed with HCl (1M, 2×100 ml), sodium hydrogen carbonate solution (2×100 ml) and brine (100mI). Evaporation of the organic layer provided the subtitled compound (22.6 g). LCMS electrospray(+ve) 259 (MH+).

Workup

  1. temperatureAfter cooling solvent
  2. customwas evaporated
  3. washwashed with HCl (1M, 2×100 ml), sodium hydrogen carbonate solution (2×100 ml) and brine (100mI)
  4. customEvaporation of the organic layer

Sources & evidence

ORD record
ord-2512ce05d94f486daac876d62248999f
Source dataset
uspto-grants-2009_09
Patent number
US07592347B2

Reaction notes

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