1-chloro-4-ethoxybutane

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

Procedure: 1-(4-Ethoxybutyl)-4-piperidone is prepared from 4-piperidone and 1-chloro-4-ethoxybutane essentially as described above in Example 38, Scheme C, step a.

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

Procedure: 1-(4-Ethoxybutyl)-4-piperidone is prepared from 4-piperidone and 1-chloro-4-ethoxybutane essentially as described above in Example 38, Scheme C, step a.

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

Procedure: Norpethidine (15.63 g, 67 mmol), 4-ethoxybutylchloride (10.67 g, 70 mmol), Na2CO3 (7.77 g, 73 mmol), KI (0.6 g) and acetonitrile (150 ml) were heated under reflux and stirring for 72 h. The mixture was filtered and the solvent removed. The residue was dissolved in diethyl ether, and the solution washed with water and dried (MgSO4). Destillation yielded 17.9 g of base boiling at 160°-163° C./0.05 mm Hg. B.p. acc. to J. Chem. Soc. 3062 (1958) 180° C./1 mm Hg. Hydrochloride m.p. 143°-145° C. under reflux The mixture was filtered the solvent removed The residue was dissolved in diethyl ether the solution washed with water dried (MgSO4) Destillation yielded 17.9 g of base boiling at 160°-163° C./0.05 mm Hg 3062 (1958) 180° C./1 mm Hg

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

Procedure: Norpethidine (15.63 g, 67 mmol), 4-ethoxybutylchloride (10.67 g, 70 mmol), Na2CO3 (7.77 g, 73 mmol), KI (0.6 g) and acetonitrile (150 ml) were heated under reflux and stirring for 72 h. The mixture was filtered and the solvent removed. The residue was dissolved in diethyl ether, and the solution washed with water and dried (MgSO4). Destillation yielded 17.9 g of base boiling at 160°-163° C./0.05 mm Hg. B.p. acc. to J. Chem. Soc. 3062 (1958) 180° C./1 mm Hg. Hydrochloride m.p. 143°-145° C. under reflux The mixture was filtered the solvent removed The residue was dissolved in diethyl ether the solution washed with water dried (MgSO4) Destillation yielded 17.9 g of base boiling at 160°-163° C./0.05 mm Hg 3062 (1958) 180° C./1 mm Hg

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

Procedure: Norpethidine (15.63 g, 67 mmol), 4-ethoxybutylchloride (10.67 g, 70 mmol), Na2CO3 (7.77 g, 73 mmol), KI (0.6 g) and acetonitrile (150 ml) were heated under reflux and stirring for 72 h. The mixture was filtered and the solvent removed. The residue was dissolved in diethyl ether, and the solution washed with water and dried (MgSO4). Destillation yielded 17.9 g of base boiling at 160°-163° C./0.05 mm Hg. B.p. acc. to J. Chem. Soc. 3062 (1958) 180° C./1 mm Hg. Hydrochloride m.p. 143°-145° C. under reflux The mixture was filtered the solvent removed The residue was dissolved in diethyl ether the solution washed with water dried (MgSO4) Destillation yielded 17.9 g of base boiling at 160°-163° C./0.05 mm Hg 3062 (1958) 180° C./1 mm Hg

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

Procedure: Norpethidine (15.63 g, 67 mmol), 4-ethoxybutylchloride (10.67 g, 70 mmol), Na2CO3 (7.77 g, 73 mmol), KI (0.6 g) and acetonitrile (150 ml) were heated under reflux and stirring for 72 h. The mixture was filtered and the solvent removed. The residue was dissolved in diethyl ether, and the solution washed with water and dried (MgSO4). Destillation yielded 17.9 g of base boiling at 160°-163° C./0.05 mm Hg. B.p. acc. to J. Chem. Soc. 3062 (1958) 180° C./1 mm Hg. Hydrochloride m.p. 143°-145° C. under reflux The mixture was filtered the solvent removed The residue was dissolved in diethyl ether the solution washed with water dried (MgSO4) Destillation yielded 17.9 g of base boiling at 160°-163° C./0.05 mm Hg 3062 (1958) 180° C./1 mm Hg

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

Procedure: Norpethidine (15.63 g, 67 mmol), 4-ethoxybutylchloride (10.67 g, 70 mmol), Na2CO3 (7.77 g, 73 mmol), KI (0.6 g) and acetonitrile (150 ml) were heated under reflux and stirring for 72 h. The mixture was filtered and the solvent removed. The residue was dissolved in diethyl ether, and the solution washed with water and dried (MgSO4). Destillation yielded 17.9 g of base boiling at 160°-163° C./0.05 mm Hg. B.p. acc. to J. Chem. Soc. 3062 (1958) 180° C./1 mm Hg. Hydrochloride m.p. 143°-145° C. under reflux The mixture was filtered the solvent removed The residue was dissolved in diethyl ether the solution washed with water dried (MgSO4) Destillation yielded 17.9 g of base boiling at 160°-163° C./0.05 mm Hg 3062 (1958) 180° C./1 mm Hg

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

Procedure: 1-(4-Ethoxybutyl)-4-piperidone is prepared from 4-piperidone and 1-chloro-4-ethoxybutane essentially as described above in Example 38, Scheme C, step a.

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

Procedure: Norpethidine (15.63 g, 67 mmol), 4-ethoxybutylchloride (10.67 g, 70 mmol), Na2CO3 (7.77 g, 73 mmol), KI (0.6 g) and acetonitrile (150 ml) were heated under reflux and stirring for 72 h. The mixture was filtered and the solvent removed. The residue was dissolved in diethyl ether, and the solution washed with water and dried (MgSO4). Destillation yielded 17.9 g of base boiling at 160°-163° C./0.05 mm Hg. B.p. acc. to J. Chem. Soc. 3062 (1958) 180° C./1 mm Hg. Hydrochloride m.p. 143°-145° C. under reflux The mixture was filtered the solvent removed The residue was dissolved in diethyl ether the solution washed with water dried (MgSO4) Destillation yielded 17.9 g of base boiling at 160°-163° C./0.05 mm Hg 3062 (1958) 180° C./1 mm Hg