Sodium Iodide → HCID 60998073, compound

HRID 520426Notes

Reaction equation

HRID 520426 reaction equation
Br[C:2]([CH3:9])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:10]1([NH2:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[CH:10]1([NH:16][C:2]([CH3:9])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7965CyclohexylamineHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester

Product 1

HCID 60998073HCID 60998073, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A stirred suspension of ethyl 2-bromo-2-methylpropanoate (0.975 g, 5 mmol), cyclohexanamine (0.496 g, 5.00 mmol), potassium carbonate (1.382 g, 10.00 mmol) and sodium iodide (0.600 g, 4.00 mmol) in acetonitrile (10 ml) was heated at 90° C. overnight under nitrogen. The reaction mixture was cooled, filtered and evaporated to dryness and then purified by silica gel FCC (5% EtOAc in DCM) to afford ethyl 2-(cyclohexylamino)-2-methylpropanoate as a clear oil (215 mg, ˜20%). 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 4.16 (q, J=7.2 Hz, 2H), 2.38-2.29 (m, 1H), 1.86-1.78 (m, 2H), 1.74-1.67 (m, J=13.5, 3.4, 3.4 Hz, 2H), 1.66-1.55 (m, 2H), 1.31 (s, 6H), 1.30-1.27 (m, 3H), 1.27-1.19 (m, 2H), 1.15-1.04 (m, 2H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. customevaporated to dryness
  4. custompurified by silica gel FCC (5% EtOAc in DCM)

Sources & evidence

ORD record
ord-7c5bc97cd91744409e180429c05059c4
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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