4-(2-aminopropyl)phenol

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

Procedure: A mixture of 7.00 g (46.6 mmol) 4-hydroxyphenylacetone and 200 mL 7N ammonia in MeOH is charged with 0.70 g Raney nickel. The mixture is stirred in an hydrogen atmosphere (50 psi) at r.t. over night. After complete reaction, the mixture is filtrated, the solvent is removed in vacuo and the crude product is purified by HPLC (MeOH/H2O/NH3). After complete reaction the mixture is filtrated the solvent is removed in vacuo the crude product is purified by HPLC (MeOH/H2O/NH3)

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: A mixture of 7.00 g (46.6 mmol) 4-hydroxyphenylacetone and 200 mL 7N ammonia in MeOH is charged with 0.70 g Raney nickel. The mixture is stirred in an hydrogen atmosphere (50 psi) at r.t. over night. After complete reaction, the mixture is filtrated, the solvent is removed in vacuo and the crude product is purified by HPLC (MeOH/H2O/NH3). After complete reaction the mixture is filtrated the solvent is removed in vacuo the crude product is purified by HPLC (MeOH/H2O/NH3)

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

Procedure: To a solution of 4-hydroxyphenylacetone (0.5 g, Avocado, U.K.) and ammonium acetate (2.54 g, Aldrich, U.S.A.) in 10 mL methanol was added 0.17 g of sodium cyanoborohydride (Aldrich, U.S.A.). After stirring for 72 h at rt, concentrated hydrochloric acid was added dropwise until the solution reached pH 2. The solvent was evaporated and the resulting residue was dissolved in water, then extracted 3 times with diethyl ether. The aqueous layer was neutralized to pH 8 by the addition of potassium hydroxide and extracted with diethyl ether. The basic ether layer was dried over sodium sulfate and the solvent was removed in vacuo to give 0.23 g of 4-(2-amino-propyl)-phenol. The solvent was evaporated the resulting residue was dissolved in water extracted 3 times with diethyl ether The aqueous layer was neutralized to pH 8 by the addition of potassium hydroxide extracted with diethyl ether The basic ether layer was dried over sodium sulfate the solvent was removed in vacuo

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

Procedure: A mixture of 7.00 g (46.6 mmol) 4-hydroxyphenylacetone and 200 mL 7N ammonia in MeOH is charged with 0.70 g Raney nickel. The mixture is stirred in an hydrogen atmosphere (50 psi) at r.t. over night. After complete reaction, the mixture is filtrated, the solvent is removed in vacuo and the crude product is purified by HPLC (MeOH/H2O/NH3). After complete reaction the mixture is filtrated the solvent is removed in vacuo the crude product is purified by HPLC (MeOH/H2O/NH3)

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

Procedure: To a solution of 4-hydroxyphenylacetone (0.5 g, Avocado, U.K.) and ammonium acetate (2.54 g, Aldrich, U.S.A.) in 10 mL methanol was added 0.17 g of sodium cyanoborohydride (Aldrich, U.S.A.). After stirring for 72 h at rt, concentrated hydrochloric acid was added dropwise until the solution reached pH 2. The solvent was evaporated and the resulting residue was dissolved in water, then extracted 3 times with diethyl ether. The aqueous layer was neutralized to pH 8 by the addition of potassium hydroxide and extracted with diethyl ether. The basic ether layer was dried over sodium sulfate and the solvent was removed in vacuo to give 0.23 g of 4-(2-amino-propyl)-phenol. The solvent was evaporated the resulting residue was dissolved in water extracted 3 times with diethyl ether The aqueous layer was neutralized to pH 8 by the addition of potassium hydroxide extracted with diethyl ether The basic ether layer was dried over sodium sulfate the solvent was removed in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1.88 g (10.0 mmol) 4-(2-amino-propyl)-phenol*HCl and 1.80 g (21.0 mmol) NaHCO3 are combined in 50 mL water and cooled down to 0° C. 0.95 mL (10.0 mmol) acetic anhydride, dissolved in 50 mL ACN, are dropped into the mixture over a period of 1.5 h. The reaction mixture is stirred at r.t. for 72 h. The ACN is evaporated in vacuo and the aq. residue is acidified with HCl (1N). The mixture is extracted several times with EtOAc. The organic layers are combined, dried with Na2SO4 and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, DCM/MeOH 95/5). are dropped into the mixture over a period of 1.5 h The ACN is evaporated in vacuo The mixture is extracted several times with EtOAc dried with Na2SO4 the solvent is removed in vacuo The crude product is purified by column chromatography (silica gel, DCM/MeOH 95/5)

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

Procedure: 5.80 g (20.0 mmol) 4-[2-(1-phenyl-ethylamino)-propyl]-phenol (I37) are added to 300 mL MeOH and charged with 0.60 g palladiumhydroxide (20%) on activated carbon. The mixture is stirred in a hydrogen atmosphere (50 psi) at 50° C. for 1 h 15 min. Then the mixture is filtrated, the solvent is removed in vacuo and the residue is triturated diethylether. The residue is dried at 80° C. in vacuo. Then the mixture is filtrated the solvent is removed in vacuo the residue is triturated diethylether The residue is dried at 80° C. in vacuo

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

Procedure: To a solution of 4-hydroxyphenylacetone (0.5 g, Avocado, U.K.) and ammonium acetate (2.54 g, Aldrich, U.S.A.) in 10 mL methanol was added 0.17 g of sodium cyanoborohydride (Aldrich, U.S.A.). After stirring for 72 h at rt, concentrated hydrochloric acid was added dropwise until the solution reached pH 2. The solvent was evaporated and the resulting residue was dissolved in water, then extracted 3 times with diethyl ether. The aqueous layer was neutralized to pH 8 by the addition of potassium hydroxide and extracted with diethyl ether. The basic ether layer was dried over sodium sulfate and the solvent was removed in vacuo to give 0.23 g of 4-(2-amino-propyl)-phenol. The solvent was evaporated the resulting residue was dissolved in water extracted 3 times with diethyl ether The aqueous layer was neutralized to pH 8 by the addition of potassium hydroxide extracted with diethyl ether The basic ether layer was dried over sodium sulfate the solvent was removed in vacuo