3-(4-chlorophenoxy)propan-1-amine

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

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

Procedure: A suspension of aluminium chloride (7.95 g) in ether (25 ml) was added to a stirred suspension of lithium aluminium chloride (2.02 g) in ether (45 ml). A solution of 3-(4-chlorophenoxy)propionitrile (10. 4 g) in ether (75 ml) was then added to the stirred suspension in a dropwise fashion over a period of 0.5 hours. The reaction mixture was allowed to reflux during the addition and was stirred for a further 0.75 hours after the addition was complete. Water (20 ml) was slowly added to the cooled reaction mixture, followed by sodium hydroxide solution (0.001M, 10 ml). The resulting precipitate was collected by filtration, washed with ethyl acetate and the filtrate dried using phase separating paper and evaporated to give 3-(4-chlorophenoxy)propylamine as an oil (7.5 g). Treatment of this oil with ethereal hydrogen chloride solution gave a solid which was recrystallised from ethanol to yield the hydrogen chloride salt of 3-(4-chlorophenoxy)propylamine as a solid (1.6 g), m.p. 182° C.; microanalysis, found: C, 48.5; H, 5.9; N, 6.3, Cl 31.6%; C9H12ONCl.HCl requires: C, 48.6; H, 5.9; N, 6.3; Cl, 32.0%. to reflux during the addition after the addition The resulting precipitate was collected by filtration washed with ethyl acetate the filtrate dried separating paper evaporated

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

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

Procedure: A suspension of aluminium chloride (7.95 g) in ether (25 ml) was added to a stirred suspension of lithium aluminium chloride (2.02 g) in ether (45 ml). A solution of 3-(4-chlorophenoxy)propionitrile (10. 4 g) in ether (75 ml) was then added to the stirred suspension in a dropwise fashion over a period of 0.5 hours. The reaction mixture was allowed to reflux during the addition and was stirred for a further 0.75 hours after the addition was complete. Water (20 ml) was slowly added to the cooled reaction mixture, followed by sodium hydroxide solution (0.001M, 10 ml). The resulting precipitate was collected by filtration, washed with ethyl acetate and the filtrate dried using phase separating paper and evaporated to give 3-(4-chlorophenoxy)propylamine as an oil (7.5 g). Treatment of this oil with ethereal hydrogen chloride solution gave a solid which was recrystallised from ethanol to yield the hydrogen chloride salt of 3-(4-chlorophenoxy)propylamine as a solid (1.6 g), m.p. 182° C.; microanalysis, found: C, 48.5; H, 5.9; N, 6.3, Cl 31.6%; C9H12ONCl.HCl requires: C, 48.6; H, 5.9; N, 6.3; Cl, 32.0%. to reflux during the addition after the addition The resulting precipitate was collected by filtration washed with ethyl acetate the filtrate dried separating paper evaporated

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

Procedure: By a similar procedure as described in Example 65, the title compound was prepared from 4,5,6,7-tetrahydrobenzimidazole-5-carboxylic acid and 3-(4-chlorophenoxy)propylamine.

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

Procedure: By a similar procedure as described in Example 65, the title compound was prepared from 4,5,6,7-tetrahydrobenzimidazole-5-carboxylic acid and 3-(4-chlorophenoxy)propylamine.

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

Procedure: By a similar procedure as described in Example 65, the title compound was prepared from 4,5,6,7-tetrahydrobenzimidazole-5-carboxylic acid and 3-(4-chlorophenoxy)propylamine.

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

Procedure: Intermediate 11 (150 mg, 0.808 mmol, 85% yield) was prepared as a white powder following the procedure described for Intermediate 9 replacing 2,6-dichlorophenol with 4-chlorophenol as starting material. LC-MS (ESI) 186 (M+H), RT=1.41 min (Method B).

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

Procedure: A suspension of aluminium chloride (7.95 g) in ether (25 ml) was added to a stirred suspension of lithium aluminium chloride (2.02 g) in ether (45 ml). A solution of 3-(4-chlorophenoxy)propionitrile (10. 4 g) in ether (75 ml) was then added to the stirred suspension in a dropwise fashion over a period of 0.5 hours. The reaction mixture was allowed to reflux during the addition and was stirred for a further 0.75 hours after the addition was complete. Water (20 ml) was slowly added to the cooled reaction mixture, followed by sodium hydroxide solution (0.001M, 10 ml). The resulting precipitate was collected by filtration, washed with ethyl acetate and the filtrate dried using phase separating paper and evaporated to give 3-(4-chlorophenoxy)propylamine as an oil (7.5 g). Treatment of this oil with ethereal hydrogen chloride solution gave a solid which was recrystallised from ethanol to yield the hydrogen chloride salt of 3-(4-chlorophenoxy)propylamine as a solid (1.6 g), m.p. 182° C.; microanalysis, found: C, 48.5; H, 5.9; N, 6.3, Cl 31.6%; C9H12ONCl.HCl requires: C, 48.6; H, 5.9; N, 6.3; Cl, 32.0%. to reflux during the addition after the addition The resulting precipitate was collected by filtration washed with ethyl acetate the filtrate dried separating paper evaporated