Methyl Ethyl Ketone → HCID 23452544, compound

HRID 1278077Notes

Reaction equation

HRID 1278077 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][CH:7]2[CH2:11][CH2:10][CH2:9][NH:8]2)=[CH:4][CH:3]=1.[CH:14]1[C:19]([C:20]([CH2:22][CH2:23][CH2:24]Cl)=[O:21])=[CH:18][CH:17]=[C:16]([F:26])[CH:15]=1.C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>C(OCC)C.O>[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][CH:7]2[CH2:11][CH2:10][CH2:9][N:8]2[CH2:24][CH2:23][CH2:22][C:20](=[O:21])[C:19]2[CH:14]=[CH:15][C:16]([F:26])=[CH:17][CH:18]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 5138807HCID 5138807, compound

Product 1

HCID 23452544HCID 23452544, compoundYield 27.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Boil 4 g of 2-(4-chlorobenzyl)pyrrolidine, 6.8 g of ω-chloro-4-fluorobutyrophenone, 4.2 g of potassium carbonate and 20 ml of methyl ethyl ketone under reflux for 68 hours. After cooling the resulting reaction mixture to ambient temperature, add 50 ml of water and 50 ml of diethyl ether. Collect the ether phase and dry it over sodium sulfate. Concentrate the dried ether phase to a brown oil before distilling it under a high vacuum to obtain 2.0 g of the title compound as viscous light-brown oil of b.p. 188° to 192° at 0.02 mm of Hg.

Workup

  1. temperatureAfter cooling
  2. customthe resulting reaction mixture to ambient temperature
  3. customCollect the ether phase
  4. dry with materialdry it over sodium sulfate
  5. concentrationConcentrate the dried ether phase to a brown oil
  6. distillationbefore distilling it under a high vacuum

Sources & evidence

ORD record
ord-7eb1c7d3a98a45c8bb4964a872a0364f
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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