Potassium Carbonate → Cyclohexanecarboxylic acid, 3,3-dimethyl-1-(4-morpholinyl)-, ethyl ester

HRID 1430277Notes

Reaction equation

HRID 1430277 reaction equation
[NH2:1][C:2]1([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[CH2:3]1.Br[CH2:16][CH2:17][O:18][CH2:19][CH2:20]Br.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O.O>[CH3:9][C:4]1([CH3:8])[CH2:5][CH2:6][CH2:7][C:2]([N:1]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:3]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 21521Bis(2-bromoethyl) etherHCID 64469579HCID 64469579, compound

Product 1

HCID 89498130Cyclohexanecarboxylic acid, 3,3-dimethyl-1-(4-morpholinyl)-, ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of EXAMPLE 145C (3.5 g) in N,N-dimethylformamide (30 mL) was added 1-bromo-2-(2-bromoethoxy)ethane (5.8 g) and K2CO3 (6.5 g). The reaction mixture was heated to 95° C. for 18 hours. The mixture was cooled to room temperature, diluted with water, and extracted with methylene chloride (3×50 mL). The combined organic layers were washed with saturated NaCl solution (1×25 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography, eluting with 4:1 petroleum ether/ethyl acetate solution, to give the title compound.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with methylene chloride (3×50 mL)
  3. washThe combined organic layers were washed with saturated NaCl solution (1×25 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 4:1 petroleum ether/ethyl acetate solution

Sources & evidence

ORD record
ord-843491c1cdf3492d9330348a9a2ff12e
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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