Dimethyl Sulfoxide → HCID 59263075, compound

HRID 881025Notes

Reaction equation

HRID 881025 reaction equation
CS(C)=O.Br[CH2:6][CH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1.[C:22]([C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)#[N:23].C(=O)([O-])[O-].[K+].[K+]>O.C1(C)C=CC=CC=1>[C:22]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:6][CH2:7][CH2:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:26][CH:25]=1)#[N:23]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 18409081tert-Butyl 4-(3-bromopropyl)piperidine-1-carboxylate

Product 1

HCID 59263075HCID 59263075, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a dimethylsulfoxide (130 mL) solution of 13.2 g of tert-butyl 4-(3-bromopropyl)-1-piperidinecarboxylate were added 5.13 g of 4-cyanophenol and 11.9 g of potassium carbonate at room temperature, which was then stirred at the same temperature for 26 hours. The reaction mixture was added to a mixture of toluene and water. The organic layer was separated, washed with a saturated sodium chloride aqueous solution, and dried with anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure to provide 14.5 g of tert-butyl 4-[3-(4-cyanophenoxy)propyl]-1-piperidinecarboxylate as white solid form.

Workup

  1. customThe organic layer was separated
  2. washwashed with a saturated sodium chloride aqueous solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. distillationby distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-eaba99cff8bc4764a8dc94cb0f63fe0e
Source dataset
uspto-grants-2015_03
Patent number
US08993603B2

Reaction notes

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