氟西汀杂质16

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The compound N,N,N',N'-tetramethyl-2-benzoyl-1,3-propanediamine (VIII) was synthesized by the method of Kinast and Tietze, Angew. Chemie. Int. Ed. 15 239-240 (1976). A mixture of 500 parts of N,N-dimethylmethylene ammonium chloride, 2600 parts of dry acetonitrile and 1035 parts of compound VII, described above, was heated to reflux under nitrogen for 15 minutes. The mixture was allowe to cool to room temperature andd then placed in the refrigerator overnight. A total of 800 parts of the hydrochloride salt of VI was isolated by filtration. The mother liquor was made basic with 10% NaOH solution and extracted with ether, the ether solution dried with anhydrous potassium carbonate and the ether evaporated under reduced pressure to yield 479 parts of a light yellow, low melting solid identified as VIII by NMR spectroscopy. The total yield of VIII was thus 93%. was heated to reflux under nitrogen for 15 minutes placed in the refrigerator overnight

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 30.0 g of acetophenone are mixed with 24.5 g of dimethylamine hydrochloride and 74.1 g of 1,3-dioxolane, 2.5 g of concentrated hydrochloric acid are added, and the mixture is heated to exactly 90° C. and maintained at that temperature for 3.5 hours. Excess dioxolane is distilled off and the residue is cooled to 0° C. The resulting 3-dimethylamino-1-phenylpropan-1-one of formula are added the mixture is heated to exactly 90° C. maintained at that temperature for 3.5 hours Excess dioxolane is distilled off

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Sodium borohydride (6.7 g) was slowly added to a solution of 3-dimethylaminopropiophenone (15.5 g) in 2-propanol (125 ml) and methanol (25 ml). After two hrs, the reaction mixture was stirred with water and extracted with ethyl acetate-ether. The organic extract was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated to give 15.2 g (97%) of 3-dimethylamino-1-phenyl-1-propanol, as an oil. A solution of 3-dimethylamino-1-phenyl-1-propanol (15 g) in dimethylformamide (75 ml) was slowly added to a suspension of sodium hydride (60% oil-dispersion, washed with hexane, 5.5 g) in dimethylformamide (20 ml). A solution of 4-fluorobenzotrifluoride (18 g) in dimethylformamide (20 ml) was added. After two hrs, the reaction mixture was stirred with ice-water and extracted with ether. The ether extract was dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated to provide 27 g (100%) of N,N-dimethyl-3-[ 4-(trifluoromethyl)phenoxy]benzenepropanamine. extracted with ethyl acetate-ether The organic extract was washed with water and saturated sodium chloride solution dried over anhydrous magnesium sulfate filtered the filtrate was evaporated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 3-Dimethylaminopropiophenone hydrochloride (20 g) was treated with aqueous sodium bicarbonate solution in dichloromethane. The layers were separated and the organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated to provide 15.8 g of 3-dimethylaminopropiophenone. The layers were separated the organic phase was dried over anhydrous magnesium sulfate filtered the filtrate was evaporated

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 21.2 g (0.2 mol) of benzaldehyde and 100 ml of absolute dimethylformamide is added dropwise in the course of 1/2 hour to a mixture of 9.8 g (0.2 mol) of NaCN and 100 ml of absolute dimethylformamide in a manner analogous to Example 3. Stirring is continued for 21/2 hours at 35° C. A solution of 26.6 g (0.15 mol) of dimethyl-β-benzoyl-ethylamine and 100 ml of absolute dimethylformamide is then slowly added dropwise in the course of 2 hours. Stirring is continued for 2 hours at the same temperature and water is then added to the reaction mixture in three times its quantity. The reaction product precipitates immediately. After cooling in an ice bath, the precipitated product is suction filtered and thoroughly washed with water. 34.3 g of crude product are isolated. 21.6 g (60.5% of the theory) of dibenzoyl ethane are isolated by recrystallisation from ethanol; m.p. 143° C. 2 hours at 35° C Stirring is then added to the reaction mixture in three times its quantity The reaction product precipitates immediately After cooling in an ice bath the precipitated product is suction filtered thoroughly washed with water 34.3 g of crude product are isolated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 21.2 g (0.2 mol) of benzaldehyde and 100 ml of absolute dimethylformamide is added dropwise in the course of 1/2 hour to a mixture of 9.8 g (0.2 mol) of NaCN and 100 ml of absolute dimethylformamide in a manner analogous to Example 3. Stirring is continued for 21/2 hours at 35° C. A solution of 26.6 g (0.15 mol) of dimethyl-β-benzoyl-ethylamine and 100 ml of absolute dimethylformamide is then slowly added dropwise in the course of 2 hours. Stirring is continued for 2 hours at the same temperature and water is then added to the reaction mixture in three times its quantity. The reaction product precipitates immediately. After cooling in an ice bath, the precipitated product is suction filtered and thoroughly washed with water. 34.3 g of crude product are isolated. 21.6 g (60.5% of the theory) of dibenzoyl ethane are isolated by recrystallisation from ethanol; m.p. 143° C. 2 hours at 35° C Stirring is then added to the reaction mixture in three times its quantity The reaction product precipitates immediately After cooling in an ice bath the precipitated product is suction filtered thoroughly washed with water 34.3 g of crude product are isolated