3-(3-methoxypropoxy)propan-1-ol

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Chloro-3-methoxy-2-methyl-pyridine (0.47 g, 3 mmol) was mixed with dipropyleneglycolmonomethylether (3 ml), piperazine (1.1 g, 7.2 mmol) and N,N-dimethylaniline (0.36 g, 3 mmol) and stirred at 140° C. for 72 hours. The solvent was removed under reduced pressure and the residue was purified by column chromatography (prepacked silica column, gradient ethyl acetate/methanol with the addition of 1% ammonia). The raw product was dissolved in 1M NaOH and extracted with a mixture of diethylether, dichloromethane and ethylacetate (1:1:1) several times. The combined organic phases were washed with water, dried over sodium sulfate, and the solvent was removed under reduced pressure to yield 585 mg of a yellow solid (2.8 g, 94%). MS (APCI): m/z=208.0 [M+1]+. The solvent was removed under reduced pressure the residue was purified by column chromatography (prepacked silica column, gradient ethyl acetate/methanol with the addition of 1% ammonia) The raw product was dissolved in 1M NaOH extracted with a mixture of diethylether, dichloromethane and ethylacetate (1:1:1) several times The combined organic phases were washed with water dried over sodium sulfate the solvent was removed under reduced pressure

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Chloroquinaldine (0.888 g, 5 mmol) and ethyl piperidine-4-carboxylate (1.18 g, 7.5 mmol) were mixed together with dipropyleneglycolmonomethylether (5 ml) and stirred at 150° C. for 48 hours. The solvent was removed under reduced pressure and the residue purified by column chromatography (pre-packed silica column, gradient of dichloromethane/ethyl acetate) to give 2.43 g of a brown oil that was used directly in the next step. MS (APCI): m/z=298.9 [M+1]+. The solvent was removed under reduced pressure the residue purified by column chromatography (pre-packed silica column, gradient of dichloromethane/ethyl acetate)

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Chloro-3-methoxy-2-methyl-pyridine (0.47 g, 3 mmol) was mixed with dipropyleneglycolmonomethylether (3 ml), piperazine (1.1 g, 7.2 mmol) and N,N-dimethylaniline (0.36 g, 3 mmol) and stirred at 140° C. for 72 hours. The solvent was removed under reduced pressure and the residue was purified by column chromatography (prepacked silica column, gradient ethyl acetate/methanol with the addition of 1% ammonia). The raw product was dissolved in 1M NaOH and extracted with a mixture of diethylether, dichloromethane and ethylacetate (1:1:1) several times. The combined organic phases were washed with water, dried over sodium sulfate, and the solvent was removed under reduced pressure to yield 585 mg of a yellow solid (2.8 g, 94%). MS (APCI): m/z=208.0 [M+1]+. The solvent was removed under reduced pressure the residue was purified by column chromatography (prepacked silica column, gradient ethyl acetate/methanol with the addition of 1% ammonia) The raw product was dissolved in 1M NaOH extracted with a mixture of diethylether, dichloromethane and ethylacetate (1:1:1) several times The combined organic phases were washed with water dried over sodium sulfate the solvent was removed under reduced pressure

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Chloro-3-methoxy-2-methyl-pyridine (0.47 g, 3 mmol) was mixed with dipropyleneglycolmonomethylether (3 ml), piperazine (1.1 g, 7.2 mmol) and N,N-dimethylaniline (0.36 g, 3 mmol) and stirred at 140° C. for 72 hours. The solvent was removed under reduced pressure and the residue was purified by column chromatography (prepacked silica column, gradient ethyl acetate/methanol with the addition of 1% ammonia). The raw product was dissolved in 1M NaOH and extracted with a mixture of diethylether, dichloromethane and ethylacetate (1:1:1) several times. The combined organic phases were washed with water, dried over sodium sulfate, and the solvent was removed under reduced pressure to yield 585 mg of a yellow solid (2.8 g, 94%). MS (APCI): m/z=208.0 [M+1]+. The solvent was removed under reduced pressure the residue was purified by column chromatography (prepacked silica column, gradient ethyl acetate/methanol with the addition of 1% ammonia) The raw product was dissolved in 1M NaOH extracted with a mixture of diethylether, dichloromethane and ethylacetate (1:1:1) several times The combined organic phases were washed with water dried over sodium sulfate the solvent was removed under reduced pressure

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Chloroquinaldine (0.888 g, 5 mmol) and ethyl piperidine-4-carboxylate (1.18 g, 7.5 mmol) were mixed together with dipropyleneglycolmonomethylether (5 ml) and stirred at 150° C. for 48 hours. The solvent was removed under reduced pressure and the residue purified by column chromatography (pre-packed silica column, gradient of dichloromethane/ethyl acetate) to give 2.43 g of a brown oil that was used directly in the next step. MS (APCI): m/z=298.9 [M+1]+. The solvent was removed under reduced pressure the residue purified by column chromatography (pre-packed silica column, gradient of dichloromethane/ethyl acetate)

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Chloro-3-methoxy-2-methyl-pyridine (0.47 g, 3 mmol) was mixed with dipropyleneglycolmonomethylether (3 ml), piperazine (1.1 g, 7.2 mmol) and N,N-dimethylaniline (0.36 g, 3 mmol) and stirred at 140° C. for 72 hours. The solvent was removed under reduced pressure and the residue was purified by column chromatography (prepacked silica column, gradient ethyl acetate/methanol with the addition of 1% ammonia). The raw product was dissolved in 1M NaOH and extracted with a mixture of diethylether, dichloromethane and ethylacetate (1:1:1) several times. The combined organic phases were washed with water, dried over sodium sulfate, and the solvent was removed under reduced pressure to yield 585 mg of a yellow solid (2.8 g, 94%). MS (APCI): m/z=208.0 [M+1]+. The solvent was removed under reduced pressure the residue was purified by column chromatography (prepacked silica column, gradient ethyl acetate/methanol with the addition of 1% ammonia) The raw product was dissolved in 1M NaOH extracted with a mixture of diethylether, dichloromethane and ethylacetate (1:1:1) several times The combined organic phases were washed with water dried over sodium sulfate the solvent was removed under reduced pressure

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Chloroquinaldine (0.888 g, 5 mmol) and ethyl piperidine-4-carboxylate (1.18 g, 7.5 mmol) were mixed together with dipropyleneglycolmonomethylether (5 ml) and stirred at 150° C. for 48 hours. The solvent was removed under reduced pressure and the residue purified by column chromatography (pre-packed silica column, gradient of dichloromethane/ethyl acetate) to give 2.43 g of a brown oil that was used directly in the next step. MS (APCI): m/z=298.9 [M+1]+. The solvent was removed under reduced pressure the residue purified by column chromatography (pre-packed silica column, gradient of dichloromethane/ethyl acetate)