Diethyl (ethoxymethylene)malonate → HCID 21192567, compound

HRID 1068033Notes

Reaction equation

HRID 1068033 reaction equation
[N:1]1([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(O[CH:24]=[C:25]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:26]([O:28][CH2:29][CH3:30])=[O:27])C>N1C=CC=CC=1>[N:1]1([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([N:14]([CH:24]=[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:12][CH:13]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 21192615HCID 21192615, compound

Product 1

HCID 21192567HCID 21192567, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
140 °C

Procedure

A flask containing N-[4-(4-morpholinylmethyl)phenyl]tetrahydro-2H-pyran-4-amine (0.34 g) is treated with diethyl ethoxymethylenemalonate (0.30 mL) and pyridine (0.20 mL). The flask is tightly capped and heated to 140° C. for 2 hours. The reaction is cooled to room temperature and azeotroped under reduced pressure with toluene (3×). The residue is dissolved in dichloromethane and washed with water, brine, dried and concentrated under reduced pressure. The residue is chromatographed on silica eluting with 2% to 6% methanol in dichloromethane. The product-containing fractions are evaporated to give 0.41 g of diethyl 2-{[4-(4-morpholinylmethyl)(tetrahydro-2H-pyran-4-yl)anilino]methylene}malonate as a tan oil.

Workup

  1. customThe flask is tightly capped
  2. temperatureThe reaction is cooled to room temperature
  3. customazeotroped under reduced pressure with toluene (3×)
  4. dissolutionThe residue is dissolved in dichloromethane
  5. washwashed with water, brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is chromatographed on silica eluting with 2% to 6% methanol in dichloromethane
  9. customThe product-containing fractions are evaporated

Sources & evidence

ORD record
ord-610da5d5d13941d293b1c97ac2ccb68f
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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