4-phenylbutanoyl chloride

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

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

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

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

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

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

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: 4-Phenylbutanoyl chloride (14.7 g.) was added dropwise to a stirred solution of diazomethane (7.5 g.) in diethyl ether (340 ml.) at 0° C. The solution was stirred in an ice bath for 1 hour further and then it was saturated with anhydrous hydrogen chloride gas. After 1 hour at 0° C, dry nitrogen was passed through this solution, which was then poured onto crushed ice (about 300 ml.). The ethereal layer was separated and the aqueous phase was diluted with water (150 ml.), saturated with sodium chloride, and extracted with diethyl ether. The combined ethereal solutions were washed with water, aqueous sodium carbonate solution (2N), and then again with water, and dried over anhydrous magnesium sulphate. The solution was evaporated and the residue was distilled, to give 1-chloro-2-oxo-5-phenylpentane (11.5 g.), b.p. 150°-151° C./10 mm.Hg (Elemental analysis: C, 67.4; H, 7.1; Cl, 18.0%; C11H13C10 requires C, 67.2; H, 6.7; Cl, 18.0%. νmax 1455 cm-1, 1500 cm-1, 1725 cm-1). After 1 hour at 0° C was then poured The ethereal layer was separated the aqueous phase was diluted with water (150 ml.), saturated with sodium chloride extracted with diethyl ether The combined ethereal solutions were washed with water, aqueous sodium carbonate solution (2N) again with water, and dried over anhydrous magnesium sulphate The solution was evaporated the residue was distilled

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

Procedure: 4-(Aminomethyl)benzoic acid (3.6 g) is suspended in methylene chloride (100 mL), to which 15 mL triethylamine is added. Chlorotrimethylsilane (10 mL) is then added and the mixture allowed to stir at room temperature for 1 hr. The mixture is then cooled in an ice bath and 4-phenylbutyryl chloride (5.3 g) in methylene chloride (10 mL) is added dropwise and the resulting mixture stirred for 30 min at 0° C., followed by an additional 3 hrs at ambient temperature. The mixture is treated with 75 mL 1 N HCl, after which the organic layer is separated and extracted with 1 N HCl. The precipitate which had formed is recovered by filtration and recrystallized two times from methanol/1 N HCl to give pure N-(4-carboxybenzyl)-4-phenylbutyramide M.p. 178°-179° C. is added The mixture is then cooled in an ice bath the resulting mixture stirred for 30 min at 0° C. followed by an additional 3 hrs at ambient temperature after which the organic layer is separated extracted with 1 N HCl The precipitate which had formed is recovered by filtration recrystallized two times from methanol/1 N HCl

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

Procedure: N-[2-(6-Amino-7-hydroxy-2,3-dihydro-1H-inden-1-yl)ethyl]acetamide hydrochloride (100 mg, 0.369 mmol) was dissolved in pyridine (4 mL), 4-phenylbutanoyl chloride (74.1 mg, 0.406 mmol) was added under ice-cooling, and the mixture was stirred for 15 min. Water was added to the reaction solution, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=80/20→100/0) to give the title compound (96.8 mg, yield 69%). cooling the solvent was evaporated under reduced pressure The residue was purified by silica gel column chromatography (ethyl acetate/hexane=80/20→100/0)

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