Water → 1-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)piperidine-3-carboxylic acid amide

HRID 2407297Notes

Reaction equation

HRID 2407297 reaction equation
Br[CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4]1.[NH:13]1[CH2:18][CH2:17][CH2:16][CH:15]([C:19]([NH2:21])=[O:20])[CH2:14]1.C([O-])([O-])=O.[K+].[K+].O>C(#N)C>[O:8]1[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4][CH:3]1[CH2:2][N:13]1[CH2:18][CH2:17][CH2:16][CH:15]([C:19]([NH2:21])=[O:20])[CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 929803-PiperidinecarboxamideHCID 983332-Bromomethyl-1,4-benzodioxane

Product 1

HCID 251759711-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)piperidine-3-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 2-bromomethyl-2,3-dihydrobenzo[1,4]dioxine (0.2 g, 0.87 mmol) and piperidine-3-carboxylic acid amide (0.13 g, 1.05 mmol) in acetonitrile (20 ml) was added K2CO3 (0.60 g, 4.36 mmol) and KI (0.72 g, 4.36 mmol). The reaction mixture was refluxed for 2 h. Water (100 ml) was then added. The reaction mixture was extracted with EtOAc (3×5 ml). The combined organic phases were dried (Na2SO4), filtered and the filtrate was evaporated to give the title compound, which was purified by column chromatography (EtOAc/heptane, 50:50).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. extractionThe reaction mixture was extracted with EtOAc (3×5 ml)
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. filtrationfiltered
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-eeb14c89589849e69d313cf647bf31eb
Source dataset
uspto-grants-2014_08
Patent number
US08809536B2

Reaction notes

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