Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 57964382, compound

HRID 2403542Notes

Reaction equation

HRID 2403542 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH:17]3[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]3)[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[CH2:26]([O:28][C:29](=[O:50])[CH:30]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:27]>C1(C)C=CC=CC=1.C(OCC)C>[CH2:26]([O:28][C:29](=[O:50])[CH:30]=[C:20]1[CH2:19][CH2:18][CH:17]([CH2:16][CH2:15][N:12]2[CH2:11][CH2:10][N:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:25])([F:1])[F:24])[CH:4]=3)[CH2:14][CH2:13]2)[CH2:22][CH2:21]1)[CH3:27]

Participants

5

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 57964668HCID 57964668, compound

Product 1

HCID 57964382HCID 57964382, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2.77 g (7.8 mmol) of 4-{2-[4-(3-trifluoromethyl-phenyl)piperazin-1-yl]ethyl}cyclohexanone (example 1, path 11, step b) and 3.13 g (9.0 mmol) of (triphenyl-λ5-phosphanylidene)acetic acid ethyl ester in 40 mL of toluene is refluxed overnight. After concentration of toluene, the residue is taken off in diethyl ether and the solid is filtered. The filtrate is concentrated and purified over 150 g of silica gel (eluant dichloromethane/heptane 98/2) to give 1.48 g (45%) of (4-{2-[4-(3-trifluoromethylphenyl)piperazin-1-yl]ethyl}cyclohexylidene)acetic acid ethyl ester as an oil.

Workup

  1. temperatureis refluxed overnight
  2. filtrationthe solid is filtered
  3. concentrationThe filtrate is concentrated
  4. custompurified over 150 g of silica gel (eluant dichloromethane/heptane 98/2)

Sources & evidence

ORD record
ord-1ef63a4be46f4b78ba547d353dc43d5f
Source dataset
uspto-grants-2014_08
Patent number
US08802678B2

Reaction notes

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