Dimethyl Sulfoxide → tert-butyl N-[1-(4-cyanophenyl)piperidin-4-yl]carbamate

HRID 350850Notes

Reaction equation

HRID 350850 reaction equation
CS(C)=O.[CH3:5][C:6]([O:9][C:10]([NH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:11])([CH3:8])[CH3:7].F[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>O>[C:24]([C:23]1[CH:26]=[CH:27][C:20]([N:16]2[CH2:15][CH2:14][CH:13]([NH:12][C:10](=[O:11])[O:9][C:6]([CH3:5])([CH3:7])[CH3:8])[CH2:18][CH2:17]2)=[CH:21][CH:22]=1)#[N:25]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 2794821tert-butyl N-[1-(4-cyanophenyl)piperidin-4-yl]carbamateYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A DMSO (25 mL, 0.1M) solution containing 4-N—BOC-aminopiperidine (500 mg, 2.5 mmol, 1.0 eq), 4-fluorobenzonitrile (303 mg, 2.5 mmol, 1.0 eq), and potassium carbonate (691 mg, 5.0 mmol, 2.0 eq) was heated to 100° C. for 18 h. The resulting mixture was cooled to RT, poured in H2O (ca 50 mL), and extracted (3×) with EtOAc. The combined extracts were washed (2×) with H2O, dried over MgSO4, and concentrated in vacuo. The resulting solid was used in the next step without further purification. Isolated 642 mg (2.13 mmol, 85% yield).

Workup

  1. temperatureThe resulting mixture was cooled to RT
  2. extractionextracted (3×) with EtOAc
  3. washThe combined extracts were washed (2×) with H2O
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting solid was used in the next step without further purification
  7. customIsolated 642 mg (2.13 mmol, 85% yield)

Sources & evidence

ORD record
ord-1fdd714202fe43748200a93890ff7cb1
Source dataset
uspto-grants-2007_02
Patent number
US07183290B2

Reaction notes

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