Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate → HCID 20373701, compound

HRID 1834515Notes

Reaction equation

HRID 1834515 reaction equation
[Na].[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:16])[CH2:10][C:11](OCC)=O)=[CH:5][CH:4]=1.[CH3:17][C:18]1([O:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:23][CH2:22][N:21]([CH2:24]C[Cl:26])[CH2:20][CH2:19]1>C1(C)C=CC=CC=1>[ClH:26].[CH3:17][C:18]1([O:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:23][CH2:22][N:21]([CH2:24][CH2:11][CH2:10][C:9]([C:6]2[CH:5]=[CH:4][C:3]([F:2])=[CH:8][CH:7]=2)=[O:16])[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 2758844Ethyl 3-(4-Fluorophenyl)-3-OxopropanoateHCID 5360545SodiumHCID 20373708HCID 20373708, compound

Product 1

HCID 20373701HCID 20373701, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

3.1 g (0.127 m) of sodium is granulated in 200 ml of boiling toluene. After cooling, 26.5 g (0.126 m) of ethyl beta-(p-fluorophenyl)-beta-oxopropionate is added drop by drop and then the solution is stirred for one-half hour at 50° C. The yellow solution which forms is cooled and 30 g (0.30 m) of beta-(4-methyl-4-butoxy-piperidino)-ethyl-chloride is added rapidly thereto. The reaction mixture is stirred for four hours at 60° C and for five hours at 85° C. After evaporation on a steam bath and addition of 500 ml of 2.5-N sulphonic acid, the solution is refluxed for sixteen hours, cooled, alkalized with an excess of potassium carbonate, and extracted with ether. The solution is evaporated and the residue distilled at 124-130/0.01 mm Hg. Yield 19.5 g. The hydrochloride has the m.p. 167°-169° C.

Workup

  1. temperatureAfter cooling
  2. temperatureThe yellow solution which forms is cooled
  3. stirringThe reaction mixture is stirred for four hours at 60° C and for five hours at 85° C
  4. customAfter evaporation on a steam bath
  5. additionaddition of 500 ml of 2.5-N sulphonic acid
  6. temperaturethe solution is refluxed for sixteen hours
  7. temperaturecooled
  8. extractionextracted with ether
  9. customThe solution is evaporated
  10. distillationthe residue distilled at 124-130/0.01 mm Hg

Sources & evidence

ORD record
ord-b87fb14b18184d07b900aca7061feb3a
Source dataset
uspto-grants-1978_01
Patent number
US04070473

Reaction notes

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