6-chloro-1-phenylhexan-1-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a 250 ml round-bottomed flask were added 5.0 g (29.65 mmol) 4-chlorophenylbutane and 10 ml 1,2-dichloroethane. To the stirred solution was added a solution of 4.35 g (32.62 mmol) aluminum chloride and 4.22 ml (59.31 mmol) acetyl chloride in 50 ml 1,2-dichloroethane. The solution evolved HCl as it was stirred at room temperature for 1 hour. It was then poured into water, the layers were separated, and the organic layer was washed with 1N HCl, aqueous sodium bicarbonate solution, and brine, dried over sodium sulfate, and evaporated to an oil, 6.7 g (>100%). NMR (CDCl3): 1.76 (m, 4H), 2.54 (m, 3H), 2.66 (m, 2H), 3.50 (m, 2H), 7.2 and 7.85 (m, 4H). IR (cm.-1, neat): 1678 (C=O). the layers were separated the organic layer was washed with 1N HCl, aqueous sodium bicarbonate solution, and brine dried over sodium sulfate evaporated to an oil, 6.7 g (>100%)

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

Procedure: To a 250 ml round-bottomed flask were added 5.0 g (29.65 mmol) 4-chlorophenylbutane and 10 ml 1,2-dichloroethane. To the stirred solution was added a solution of 4.35 g (32.62 mmol) aluminum chloride and 4.22 ml (59.31 mmol) acetyl chloride in 50 ml 1,2-dichloroethane. The solution evolved HCl as it was stirred at room temperature for 1 hour. It was then poured into water, the layers were separated, and the organic layer was washed with 1N HCl, aqueous sodium bicarbonate solution, and brine, dried over sodium sulfate, and evaporated to an oil, 6.7 g (>100%). NMR (CDCl3): 1.76 (m, 4H), 2.54 (m, 3H), 2.66 (m, 2H), 3.50 (m, 2H), 7.2 and 7.85 (m, 4H). IR (cm.-1, neat): 1678 (C=O). the layers were separated the organic layer was washed with 1N HCl, aqueous sodium bicarbonate solution, and brine dried over sodium sulfate evaporated to an oil, 6.7 g (>100%)

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

Procedure: To a 250 ml round-bottomed flask were added 5.0 g (29.65 mmol) 4-chlorophenylbutane and 10 ml 1,2-dichloroethane. To the stirred solution was added a solution of 4.35 g (32.62 mmol) aluminum chloride and 4.22 ml (59.31 mmol) acetyl chloride in 50 ml 1,2-dichloroethane. The solution evolved HCl as it was stirred at room temperature for 1 hour. It was then poured into water, the layers were separated, and the organic layer was washed with 1N HCl, aqueous sodium bicarbonate solution, and brine, dried over sodium sulfate, and evaporated to an oil, 6.7 g (>100%). NMR (CDCl3): 1.76 (m, 4H), 2.54 (m, 3H), 2.66 (m, 2H), 3.50 (m, 2H), 7.2 and 7.85 (m, 4H). IR (cm.-1, neat): 1678 (C=O). the layers were separated the organic layer was washed with 1N HCl, aqueous sodium bicarbonate solution, and brine dried over sodium sulfate evaporated to an oil, 6.7 g (>100%)

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Prepared by Procedure K and Scheme B1 using 6-chloro-1-phenyl-1-hexanone and 2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide: Anal. Calcd for C27H36N2O2+0.1CHCl3: C, 75.3; H, 8.39; N, 6.46. Found: C, 75.4; H, 7.89; N, 6.18; ESMS m/e: 421.1 (M+H)+. Prepared by Procedure K and Scheme B1

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

Procedure: Prepared by Procedure K and Scheme B1 using 6-chloro-1-phenyl-1-hexanone and 2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide: Anal. Calcd for C27H36N2O2+0.1CHCl3: C, 75.3; H, 8.39; N, 6.46. Found: C, 75.4; H, 7.89; N, 6.18; ESMS m/e: 421.1 (M+H)+. Prepared by Procedure K and Scheme B1

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

Procedure: To a 250 ml round-bottomed flask were added 5.0 g (29.65 mmol) 1-chloro-4-phenylbutane and 10 ml 1,2-dichloroethane. To the stirred solution was added a solution of 4.35 g (32.62 mmol) aluminum chloride and 4.22 ml (59.31 mmol) acetyl chloride in 50 ml 1,2-dichloroethane. The solution evolved HCl as it was stirred at room temperature for 1 hour. It was then poured into water, the layers separated, and the organic layer washed with 1N HCl, aqueous sodium bicarbonate solution, brine, dried over sodium sulfate, and evaporated to an oil, 6.7 g (>100%). NMR (delta, CDCl3): 1.76 (m, 4H), ~2.5 (s, 3H), 3.50 (m, 2H), 7.2 and 7.85 (m, 4H). IR cm-1, neat): 1678 (C =O). the layers separated the organic layer washed with 1N HCl, aqueous sodium bicarbonate solution, brine dried over sodium sulfate evaporated to an oil, 6.7 g (>100%)

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

Procedure: Aluminum chloride (16 g, 0.12 mol) is suspended in carbon tetrachloride (80 ml) and 6-chlorohexanoyl chloride (20 g, 0.12 mol) is added dropwise to the suspension with ice-cooling. After completion of addition, the mixture is stirred for 15 minutes and benzene (7.8 g, 0.1 mol) is added dropwise to the mixture with ice-cooling. After stirring with ice-cooling for 1 hour, the mixture is poured into ice-hydrochloric acid and extracted with carbon tetrachloride. The carbon tetrachloride extract is washed with water, saturated aqueous sodium bicarbonate, water and then saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The dried solution is distilled to obtain 5-chloropentyl phenyl ketone (7.3 g), b.p. 143°-150° C./0.5 mmHg. cooling After completion of addition cooling After stirring with ice- cooling for 1 hour extracted with carbon tetrachloride The carbon tetrachloride extract is washed with water, saturated aqueous sodium bicarbonate, water saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate The dried solution is distilled

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

Procedure: To a 250 ml round-bottomed flask were added 5.0 g (29.65 mmol) 1-chloro-4-phenylbutane and 10 ml 1,2-dichloroethane. To the stirred solution was added a solution of 4.35 g (32.62 mmol) aluminum chloride and 4.22 ml (59.31 mmol) acetyl chloride in 50 ml 1,2-dichloroethane. The solution evolved HCl as it was stirred at room temperature for 1 hour. It was then poured into water, the layers separated, and the organic layer washed with 1N HCl, aqueous sodium bicarbonate solution, brine, dried over sodium sulfate, and evaporated to an oil, 6.7 g (>100%). NMR (delta, CDCl3): 1.76 (m, 4H), ~2.5 (s, 3H), 3.50 (m, 2H), 7.2 and 7.85 (m, 4H). IR cm-1, neat): 1678 (C=O). the layers separated the organic layer washed with 1N HCl, aqueous sodium bicarbonate solution, brine dried over sodium sulfate evaporated to an oil, 6.7 g (>100%)