Potassium Carbonate → HCID 66746563, compound

HRID 2279414Notes

Reaction equation

HRID 2279414 reaction equation
Br[CH2:2][C:3]([CH:5]1[CH2:7][CH2:6]1)=[O:4].[C:8]([O:12][C:13](=[O:21])[NH:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)([CH3:11])([CH3:10])[CH3:9].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:8]([O:12][C:13](=[O:21])[NH:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:2][C:3]([CH:5]2[CH2:7][CH2:6]2)=[O:4])[CH2:17][CH2:16]1)([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 109208412-Bromo-1-cyclopropylethan-1-one

Product 1

HCID 66746563HCID 66746563, compoundYield 104.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-Bromo-1-cyclopropyl-ethanone (244 mg, 1.44 mmol, 1.0 eq) is added at room temperature to a stirred solution of piperidin-4-yl-carbamic acid tert-butyl ester (300 mg, 1.44 mmol, 1.0 eq) in N,N-dimethylformamide (12 mL), followed by potassium carbonate (200 mg, 1.44 mmol, 1.0 eq). After 4 hours stirring at 60° C., solvent is evaporated and the residue is extracted with dichloromethane (3×30 mL) and water (30 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford [1-(2-cyclopropyl-2-oxo-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester as a light yellow solid (425 mg, 99% yield).

Workup

  1. customsolvent is evaporated
  2. extractionthe residue is extracted with dichloromethane (3×30 mL) and water (30 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-946a701f6d3b46e783322449faa48278
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

Loading…