N-phenylpiperidine-4-carboxamide

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 solution of 100 mg (0.32 mmoles) of 6-bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile and 230 mg (0.96 mmoles) of piperidine-4-carboxylic acid phenylamide in 5 ml of DMF, 130 mg (0.96 mmoles) of K2CO3 is added at ambient temperature. The reaction mixture is stirred for 18 hours at ambient temperature. The reaction mixture is quenched with H2O and extracted with AcOEt. The combined extracts are washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give 130 mg of disired 1-[2-cyano-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-6-ylmethyl]-piperidine-4-carboxylic acid phenylamide in 95% yield. The reaction mixture is quenched with H2O extracted with AcOEt The combined extracts are washed with brine dried over MgSO4 concentrated under reduced pressure The residue is purified by silica gel column chromatography

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

Procedure: To a solution of 100 mg (0.32 mmoles) of 6-bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile and 230 mg (0.96 mmoles) of piperidine-4-carboxylic acid phenylamide in 5 ml of DMF, 130 mg (0.96 mmoles) of K2CO3 is added at ambient temperature. The reaction mixture is stirred for 18 hours at ambient temperature. The reaction mixture is quenched with H2O and extracted with AcOEt. The combined extracts are washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give 130 mg of disired 1-[2-cyano-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-6-ylmethyl]-piperidine-4-carboxylic acid phenylamide in 95% yield. The reaction mixture is quenched with H2O extracted with AcOEt The combined extracts are washed with brine dried over MgSO4 concentrated under reduced pressure The residue is purified by silica gel column chromatography

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

Procedure: The general procedures of Examples 1 and 2 are repeated. The compound 4-methoxy-N-methyl-2-nitrodiphenylamine is prepared and reduced to the corresponding 2-amino derivative which is converted to 5'-methoxy-1-methyl-2'-(N-methylanilino)isonipecotanilide. This isonipecotanilide base is treated with phosphorus pentoxide/phosphorus oxychloride, the cyclized product is isolated and purified and 8-methoxy-5-methyl-11-(1-methyl-4-piperidyl)-5H-dibenzo[b,e]-[1,4]diazepine is obtained. the cyclized product is isolated purified

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

Procedure: The general procedures of Examples 1 and 2 are repeated. The compound 4-methoxy-N-methyl-2-nitrodiphenylamine is prepared and reduced to the corresponding 2-amino derivative which is converted to 5'-methoxy-1-methyl-2'-(N-methylanilino)isonipecotanilide. This isonipecotanilide base is treated with phosphorus pentoxide/phosphorus oxychloride, the cyclized product is isolated and purified and 8-methoxy-5-methyl-11-(1-methyl-4-piperidyl)-5H-dibenzo[b,e]-[1,4]diazepine is obtained. the cyclized product is isolated purified

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

Procedure: To a solution of 100 mg (0.32 mmoles) of 6-bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile and 230 mg (0.96 mmoles) of piperidine-4-carboxylic acid phenylamide in 5 ml of DMF, 130 mg (0.96 mmoles) of K2CO3 is added at ambient temperature. The reaction mixture is stirred for 18 hours at ambient temperature. The reaction mixture is quenched with H2O and extracted with AcOEt. The combined extracts are washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give 130 mg of disired 1-[2-cyano-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-6-ylmethyl]-piperidine-4-carboxylic acid phenylamide in 95% yield. The reaction mixture is quenched with H2O extracted with AcOEt The combined extracts are washed with brine dried over MgSO4 concentrated under reduced pressure The residue is purified by silica gel column chromatography

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

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

Procedure: 4-(N-phenylcarbamoyl)pyridine [75.0 g, prepared as in Chem. Abs., 2013h (1958)] was hydrogenated in acetic acid (800 ml) using a platinum oxide catalyst at 50 p.s.i./30°. The catalyst was then removed by filtration, the solution evaporated, the residue basified to about pH 12 with sodium hydroxide, extracted with chloroform, and the organic extract discarded. The aqueous phase was evaporated to dryness, the residue boiled with chloroform, filtered and evaporated to leave 4-(N-phenylcarbamoyl)piperidine (17.0 g), m.p. 121°-127°. The hydrochloride salt, m.p. 231°-233°, was prepared in isopropanol from the free base and hydrogen chloride, and was recrystallised from isopropanol/ethyl acetate. 30° The catalyst was then removed by filtration the solution evaporated extracted with chloroform the organic extract The aqueous phase was evaporated to dryness filtered evaporated

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

Procedure: The general procedures of Examples 1 and 2 are repeated. The compound 4-methoxy-N-methyl-2-nitrodiphenylamine is prepared and reduced to the corresponding 2-amino derivative which is converted to 5'-methoxy-1-methyl-2'-(N-methylanilino)isonipecotanilide. This isonipecotanilide base is treated with phosphorus pentoxide/phosphorus oxychloride, the cyclized product is isolated and purified and 8-methoxy-5-methyl-11-(1-methyl-4-piperidyl)-5H-dibenzo[b,e]-[1,4]diazepine is obtained. the cyclized product is isolated purified

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

Procedure: To a solution of 100 mg (0.32 mmoles) of 6-bromomethyl-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile and 230 mg (0.96 mmoles) of piperidine-4-carboxylic acid phenylamide in 5 ml of DMF, 130 mg (0.96 mmoles) of K2CO3 is added at ambient temperature. The reaction mixture is stirred for 18 hours at ambient temperature. The reaction mixture is quenched with H2O and extracted with AcOEt. The combined extracts are washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give 130 mg of disired 1-[2-cyano-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-6-ylmethyl]-piperidine-4-carboxylic acid phenylamide in 95% yield. The reaction mixture is quenched with H2O extracted with AcOEt The combined extracts are washed with brine dried over MgSO4 concentrated under reduced pressure The residue is purified by silica gel column chromatography