Methyl Ethyl Ketone → Ethyl 2-acetyl-5-{4-[(4-fluorophenyl)phenylmethylene]piperidino}pentanoate

HRID 1089761Notes

Reaction equation

HRID 1089761 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.C([CH:24]([CH2:31][CH2:32]Cl)[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])(=O)C.C(=O)([O-])[O-].[Na+].[Na+].[CH3:40][C:41](=[O:44])CC>>[C:41]([CH:25]([CH2:24][CH2:31][CH2:32][N:12]1[CH2:11][CH2:10][C:9](=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:14][CH2:13]1)[C:26]([O:28][CH2:29][CH3:30])=[O:27])(=[O:44])[CH3:40]

Participants

5

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 10340Sodium CarbonateHCID 150203584-[(4-Fluorophenyl)(phenyl)methylidene]piperidineHCID 19915760HCID 19915760, compound

Product 1

HCID 54340777Ethyl 2-acetyl-5-{4-[(4-fluorophenyl)phenylmethylene]piperidino}pentanoate

Procedure

0.019 mol of 4-[(4-fluorophenyl)phenylmethylene]piperidine, 0.019 mol of ethyl 3-acetyl-5-chloropentanoate, blocked in cyclic form (Chem. Ber. (1967), 100, p. 1675-1679), and 2.03 g of sodium carbonate in 80 ml of 2-butanone are brought to reflux. After evaporation of the solvent, the residue is taken up in water and extracted with dichloromethane. Deprotection is then performed according to the method described in Chem. Ber. (1967), 100, p. 1675-1679.

Workup

  1. temperatureto reflux
  2. customAfter evaporation of the solvent
  3. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-23f98258b0de41449eeba4972f7e8870
Source dataset
uspto-grants-1992_01
Patent number
US05079249

Reaction notes

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