2-[2-(dimethylamino)ethoxy]-N,N-dimethylethanamine

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 process for preparing bis[2-(N,N-dimethylamino)ethyl]ether which comprises (i) contacting 2-(N,N-dimethylamino)ethanol with diethyl carbonate under conditions effective to produce bis[2-(N,N-dimethylamino)ethyl]carbonate, and (ii) contacting bis[2-(N,N-dimethylamino)ethyl]-carbonate with a magnesium:aluminum mixed metal oxide catalyst under conditions effective to produce bis[2-(N,N-dimethylamino)ethyl]ether.

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

Procedure: A process for preparing bis[2-(N,N-dimethylamino)ethyl]ether which comprises (i) contacting 2-(N,N-dimethylamino)ethanol with diethyl carbonate under conditions effective to produce bis[2-(N,N-dimethylamino)ethyl]carbonate, and (ii) contacting bis[2-(N,N-dimethylamino)ethyl]-carbonate with a magnesium:aluminum mixed metal oxide catalyst under conditions effective to produce bis[2-(N,N-dimethylamino)ethyl]ether.

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

Procedure: A process for preparing bis[2-(N,N-dimethylamino)ethyl]ether which comprises (i) contacting 2-(N,N-dimethylamino)ethanol with diethyl carbonate under conditions effective to produce bis[2-(N,N-dimethylamino)ethyl]carbonate, and (ii) contacting bis[2-(N,N-dimethylamino)ethyl]-carbonate with a magnesium:aluminum mixed metal oxide catalyst under conditions effective to produce bis[2-(N,N-dimethylamino)ethyl]ether.

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

Procedure: A process for preparing bis[2-(N,N-dimethylamino)ethyl]ether which comprises (i) contacting 2-(N,N-dimethylamino)ethanol with diethyl carbonate under conditions effective to produce bis[2-(N,N-dimethylamino)ethyl]carbonate, and (ii) contacting bis[2-(N,N-dimethylamino)ethyl]-carbonate with a magnesium:aluminum mixed metal oxide catalyst under conditions effective to produce bis[2-(N,N-dimethylamino)ethyl]ether.

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

Procedure: Bis[2-(N,N-dimethylamino)ethyl]ether (4.1 mL, 25.7 mmol) was dissolved in THF (15 mL), 2 mol/L isopropylmagnesium chloride-THF solution (13.0 mL, 25.7 mmol) was added dropwise under ice-cooling, and the mixture was stirred at room temperature for 5 min. A suspension (5 mL) of 7-benzylamino-3-bromo-6-(4-phenylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyrimidine (1.4 g, 2.9 mmol) obtained in step 4 in THF was added to this mixture under ice-cooling, and the mixture was stirred at room temperature for 2 hr. Carbon dioxide gas was bubbled into the reaction mixture for 30 min under ice-cooling, and the reaction mixture was added dropwise to ice-cooled 1 mol/L hydrochloric acid (100 mL). The mixture was stirred at room temperature for 1 hr, and the precipitate was collected by filtration, and washed with water (50 mL) to give the title compound (0.9 g, 67%). cooling cooling the mixture was stirred at room temperature for 2 hr Carbon dioxide gas was bubbled into the reaction mixture for 30 min under ice- cooling the reaction mixture was added dropwise to ice- cooled 1 mol/L hydrochloric acid (100 mL) The mixture was stirred at room temperature for 1 hr the precipitate was collected by filtration washed with water (50 mL)

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

Procedure: A process for preparing bis[2-(N,N-dimethylamino)ethyl]ether which comprises (i) contacting 2-(N,N-dimethylamino)ethanol with diethyl carbonate under conditions effective to produce bis[2-(N,N-dimethylamino)ethyl]carbonate, and (ii) contacting bis[2-(N,N-dimethylamino)ethyl]-carbonate with a magnesium:aluminum mixed metal oxide catalyst under conditions effective to produce bis[2-(N,N-dimethylamino)ethyl]ether.

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

Procedure: A process for preparing bis[2-(N,N-dimethylamino)ethyl]ether which comprises (i) contacting 2-(N,N-dimethylamino)ethanol with diethyl carbonate under conditions effective to produce bis[2-(N,N-dimethylamino)ethyl]carbonate, and (ii) contacting bis[2-(N,N-dimethylamino)ethyl]-carbonate with a magnesium:aluminum mixed metal oxide catalyst under conditions effective to produce bis[2-(N,N-dimethylamino)ethyl]ether.

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

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

Procedure: Isopropylmagnesium chloride (27.8 mL, 2 M in THF, 55.6 mmol) was added to a solution of bis(2-dimethylaminoethyl)ether (10.5 mL, 55.6 mmol) in THF (230 mL) 15° C. After 20 minutes, (4-iodophenyl)-(morpholino)methanone (14.7 g, 46.4 mmol) was added and the reaction was removed from the cooling bath. After 1 hr, another 0.8 eq of isopropylmagnesium chloride was added. Trimethyl borate (10.6, 93 mmol) was added after 15 minutes, and after stirring 40 min, the reaction was quenched with 150 ml 1 N aqueous HCl. After stirring at room temperature for 2 hr, THF was removed on the rotary evaporator and the residue was extracted three times with EtOAc. The organic extracts were dried with Na2SO4. The solvent was removed and the residue was twice suspended in toluene and the solvent removed on the rotary evaporator. The resulting white solid was suspended in hexane and this was heated at reflux for 5 minutes. After cooling to room temperature, the white solid was collected by filtration and air-dried to afford 4-(morpholine-4-carbonyl)phenylboronic acid (8.7 g). MS (ESI) m/z 236.1 (M+H). 1H NMR (MeOD) δ ppm 7.78 (2H, d, J=7.30 Hz), 7.36 (2H, d, J=8.06 Hz), 3.72-3.41 (8H, m). the reaction was removed from the cooling bath After 1 hr the reaction was quenched with 150 ml 1 N aqueous HCl After stirring at room temperature for 2 hr THF was removed on the rotary evaporator the residue was extracted three times with EtOAc The organic extracts were dried with Na2SO4 The solvent was removed the solvent removed on the rotary evaporator this was heated at reflux for 5 minutes the white solid was collected by filtration air-dried

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

Procedure: Isopropylmagnesium chloride (27.8 mL, 2 M in THF, 55.6 mmol) was added to a solution of bis(2-dimethylaminoethyl)ether (10.5 mL, 55.6 mmol) in THF (230 mL) 15° C. After 20 minutes, (4-iodophenyl)-(morpholino)methanone (14.7 g, 46.4 mmol) was added and the reaction was removed from the cooling bath. After 1 hr, another 0.8 eq of isopropylmagnesium chloride was added. Trimethyl borate (10.6, 93 mmol) was added after 15 minutes, and after stirring 40 min, the reaction was quenched with 150 ml 1 N aqueous HCl. After stirring at room temperature for 2 hr, THF was removed on the rotary evaporator and the residue was extracted three times with EtOAc. The organic extracts were dried with Na2SO4. The solvent was removed and the residue was twice suspended in toluene and the solvent removed on the rotary evaporator. The resulting white solid was suspended in hexane and this was heated at reflux for 5 minutes. After cooling to room temperature, the white solid was collected by filtration and air-dried to afford 4-(morpholine-4-carbonyl)phenylboronic acid (8.7 g). MS (ESI) m/z 236.1 (M+H). 1H NMR (MeOD) δ ppm 7.78 (2H, d, J=7.30 Hz), 7.36 (2H, d, J=8.06 Hz), 3.72-3.41 (8H, m). the reaction was removed from the cooling bath After 1 hr the reaction was quenched with 150 ml 1 N aqueous HCl After stirring at room temperature for 2 hr THF was removed on the rotary evaporator the residue was extracted three times with EtOAc The organic extracts were dried with Na2SO4 The solvent was removed the solvent removed on the rotary evaporator this was heated at reflux for 5 minutes the white solid was collected by filtration air-dried