Ethyl cyanoacetate → HCID 86701181, compound

HRID 2206300Notes

Reaction equation

HRID 2206300 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([OH:10])=[CH:4][C:3]=2[O:2]1.[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([F:21])[C:19]=1[F:20])[CH:15]=O.[C:22]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])#[N:23].N1CCCCC1>C(O)C.O>[CH2:28]([O:27][C:25]([C:24]1[CH:15]([C:14]2[CH:13]=[C:12]([F:11])[C:19]([F:20])=[C:18]([F:21])[CH:17]=2)[C:6]2[CH:7]=[C:8]3[O:9][CH2:1][O:2][C:3]3=[CH:4][C:5]=2[O:10][C:22]=1[NH2:23])=[O:26])[CH3:29]

Participants

7

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 68289SesamolHCID 27769543,4,5-Trifluorobenzaldehyde

Product 1

HCID 86701181HCID 86701181, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

3,4-Methylenedioxyphenol (166 mg, 1.2 mmol), 3,4,5-trifluorobenzaldehyde (160 mg, 1 mmol) and ethyl cyanoacetate (113 mg, 1 mmol) were taken in 7 ml ethanol at room temperature, charged with piperidine (50 μL) and then stirred at 80° C. under LC-MS control till the reaction was complete. The reaction mixture was cooled down to room temperature, diluted with water to about 15 ml, stirred for 1 h, solids were collected by filtration, washed with 60% aq. ethanol and dried (280 mg, 0.71 mmol, 71%).

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. stirringstirred for 1 h
  3. filtrationsolids were collected by filtration
  4. washwashed with 60% aq. ethanol
  5. customdried (280 mg, 0.71 mmol, 71%)

Sources & evidence

ORD record
ord-85c68d679c124f7e9a933bcca4e59b71
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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