triethoxymethylbenzene

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

Procedure: Prepared from 5-butyryl-2-indolinone, acetic anhydride and triethyl orthobenzoate Rf=0.79 (silica gel, ethyl acetate/cyclohexane/methanol 9:9:2)

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

Procedure: Prepared from 5-hexanoyl-2-indolinone, acetic anhydride and triethyl orthobenzoate Rf=0.72 (methylene chloride/methanol 30:1)

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

Procedure: Prepared from 5-propionyl-2-indolinone, acetic anhydride and triethyl orthobenzoate Rf=0.79 (silica gel, ethyl acetate/cyclohexane/methanol 9:9:2)

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

Procedure: Prepared from 5-isobutyryl-2-indolinone, acetic anhydride and triethyl orthobenzoate Rf=0.55 (silica gel, ethyl acetate/cyclohexane/methanol 9:9:2)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10 g (49 mmol) 5-butyryl-2-indolinone (Ex. I.2) in 200 ml acetic anhydride are stirred for 5 h at 130° C. Then 35 ml triethyl orthobenzoate are added and the mixture is stirred for a further 4 h at 100° C. It is then evaporated down and the resulting precipitate is suction filtered, washed and dried. It is then evaporated down filtered washed dried

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

Procedure: Prepared from 1-acetyl-5-benzoyl-2-indolinone and triethyl orthobenzoate

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

Procedure: Prepared from 1-acetyl-5-hexanoyl-2-indolinone and triethyl orthobenzoate

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

Procedure: Prepared from 1-acetyl-6-methoxy-2-indolinone, triethyl orthobenzoate and acetic anhydride

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

Procedure: 10.0 g of 1-acetyl-5,6-dimethoxy-2-indolinone, 29.2 ml of triethyl orthobenzoate and 100 ml of acetic anhydride are stirred for 48 hours at 120° C. The solvent is eliminated and the residue evaporated with toluene, combined with ether and the precipitate formed (starting compounds is suction filtered. The filtrate is concentrated by evaporation and separated through a silica gel column with toluene, then with toluene/ethyl acetate (10:1). The product is triturated with ether, suction filtered and dried in vacuo at 100° C. the residue evaporated with toluene the precipitate formed ( filtered The filtrate is concentrated by evaporation separated through a silica gel column with toluene The product is triturated with ether, suction filtered dried in vacuo at 100° C.

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

Procedure: 10.0 g of 1-acetyl-5,6-dimethoxy-2-indolinone, 29.2 ml of triethyl orthobenzoate and 100 ml of acetic anhydride are stirred for 48 hours at 120° C. The solvent is eliminated and the residue evaporated with toluene, combined with ether and the precipitate formed (starting compounds is suction filtered. The filtrate is concentrated by evaporation and separated through a silica gel column with toluene, then with toluene/ethyl acetate (10:1). The product is triturated with ether, suction filtered and dried in vacuo at 100° C. the residue evaporated with toluene the precipitate formed ( filtered The filtrate is concentrated by evaporation separated through a silica gel column with toluene The product is triturated with ether, suction filtered dried in vacuo at 100° C.

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

Procedure: A mixture of 60 mg (0.12 mmol) of tert-butyl (3RS,4RS)-4-(4-hydrazinocarbonylmethyl-phenyl)-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate and 27.7 gl (0.12 mmol) of triethyl orthobenzoate in 5 ml of ethanol was boiled under reflux for 18 hours. After cooling the mixture was evaporated under reduced pressure and the residue was chromatographed on silica gel using a 2:1 mixture of hexane and ethyl acetate as the eluent. There were obtained 30 mg (44% of theory) or tert-butyl (3RS,4RS)-3-(naphthalen-2-ylmethoxy)-4-[4-(5-phenyl-[1,3,4]oxadiazol-2-ylmethyl)-phenyl]-piperidine-1-carboxylate as a colourless foam; MS: 575 (M+H)+. under reflux for 18 hours After cooling the mixture was evaporated under reduced pressure the residue was chromatographed on silica gel using a 2:1 mixture of hexane and ethyl acetate as the eluent

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

Procedure: A mixture of 60 mg (0.12 mmol) of tert-butyl (3RS,4RS)-4-(4-hydrazinocarbonylmethyl-phenyl)-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate and 27.7 gl (0.12 mmol) of triethyl orthobenzoate in 5 ml of ethanol was boiled under reflux for 18 hours. After cooling the mixture was evaporated under reduced pressure and the residue was chromatographed on silica gel using a 2:1 mixture of hexane and ethyl acetate as the eluent. There were obtained 30 mg (44% of theory) or tert-butyl (3RS,4RS)-3-(naphthalen-2-ylmethoxy)-4-[4-(5-phenyl-[1,3,4]oxadiazol-2-ylmethyl)-phenyl]-piperidine-1-carboxylate as a colourless foam; MS: 575 (M+H)+. under reflux for 18 hours After cooling the mixture was evaporated under reduced pressure the residue was chromatographed on silica gel using a 2:1 mixture of hexane and ethyl acetate as the eluent