Potassium Carbonate → HCID 84002672, compound

HRID 509913Notes

Reaction equation

HRID 509913 reaction equation
Cl.[C:2]([O:6][C:7](=[O:15])[NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]1)([CH3:5])([CH3:4])[CH3:3].I[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][N:11]1[CH2:12][CH2:13][CH2:14][CH:9]([NH:8][C:7]([O:6][C:2]([CH3:5])([CH3:3])[CH3:4])=[O:15])[CH2:10]1)[CH3:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12183Ethyl iodoacetateHCID 44891089tert-Butyl piperidin-3-ylcarbamate--hydrogen chloride (1/1)

Product 1

HCID 84002672HCID 84002672, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of piperidin-3-yl-carbamic acid tert-butyl ester hydrochloride (1.0 g, 4.2 mmol) and ethyl iodoacetate (0.99 g, 4.6 mmol) in acetonitrile (30 mL) is added K2CO3 (1.5 g, 10.5 mmol) and the mixture stirred overnight at room temperature. Volatiles are evaporated under reduced pressure and the residue taken up with water and extracted twice with ethyl acetate. The organic phase is dried over MgSO4 and evaporated under reduced pressure. The resulting material is purified via chromatography over silica gel eluting with a mixture of EtOAc/MeOH (95:5 v/v). Yield: 0.8 g.

Workup

  1. customVolatiles are evaporated under reduced pressure
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe organic phase is dried over MgSO4
  4. customevaporated under reduced pressure
  5. customThe resulting material is purified via chromatography over silica gel eluting with a mixture of EtOAc/MeOH (95:5 v/v)

Sources & evidence

ORD record
ord-d42b9bcf75dd469d83693c66624f7a86
Source dataset
uspto-grants-2015_08
Patent number
US09096548B2

Reaction notes

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