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

HRID 1460450Notes

Reaction equation

HRID 1460450 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-454019243bb04d40a82da9633a6fe88d
Source dataset
uspto-grants-1991_12
Patent number
US05071847

Reaction notes

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