6-chloro-1-(4-fluorophenyl)hexan-1-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared by Procedure K and Scheme E using K2CO3 instead of Na2CO3 and NaI instead of KI and 6-chloro-1-(4-fluorophenyl)-1-hexanone and 2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide: ESMS m/e: 439.1 (M+H)+. Prepared by Procedure K and Scheme E

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared by Procedure K and Scheme E using K2CO3 instead of Na2CO3 and NaI instead of KI and 6-chloro-1-(4-fluorophenyl)-1-hexanone and 2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide: ESMS m/e: 439.1 (M+H)+. Prepared by Procedure K and Scheme E

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 6-chloro-1-(4-fluorophenyl)-1-hexanone (0.018 mol), intermediate 1 (0.015 mol), Na2CO3 (4 g) and potassium iodide (catalytic quantity) in methyl isobutyl ketone (200 ml) was stirred and refluxed overnight and then cooled to room temperature. The solvent was evaporated. The residue was washed with H2O and the mixture was extracted with CH2Cl2. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5). The pure fractions were collected and the solvent was evaporated. The residue was converted into the (E)-2-butenedioic acid salt (1:1); The precipitate was filtered off and dried, yielding 5.1 g 1-(4-fluorophenyl)-6-(1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridin-2-yl)-1-hexanone (E)-2-butenedioate (1:1) (71%). refluxed overnight The solvent was evaporated The residue was washed with H2O the mixture was extracted with CH2Cl2 The organic layer was separated dried filtered the solvent was evaporated The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5) The pure fractions were collected the solvent was evaporated The precipitate was filtered off dried