2-(3-chlorophenyl)butanenitrile

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

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

Procedure: rac-2-[1-(3-Chloro-phenyl)-propyl]-4,5-dihydro-1H-imidazole was prepared from 2-(3-chloro-phenyl)-butyronitrile and ethylene diamine in analogy to Example 22: colourless powder;MS (ISP): 223.0 ((M+H)+.).

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

Procedure: rac-2-[1-(3-Chloro-phenyl)-propyl]-4,5-dihydro-1H-imidazole was prepared from 2-(3-chloro-phenyl)-butyronitrile and ethylene diamine in analogy to Example 22: colourless powder;MS (ISP): 223.0 ((M+H)+.).

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

Procedure: rac-2-(3-chloro-phenyl)-butyronitrile was prepared from rac-1-(1-bromo-propyl)-3-chloro-benzene and trimethylsilyl cyanide in analogy to Example 23 c): colourless oil.

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

Procedure: rac-2-(3-chloro-phenyl)-butyronitrile was prepared from rac-1-(1-bromo-propyl)-3-chloro-benzene and trimethylsilyl cyanide in analogy to Example 23 c): colourless oil.

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

Procedure: rac-2-[1-(3-Chloro-phenyl)-propyl]-4,5-dihydro-1H-imidazole was prepared from 2-(3-chloro-phenyl)-butyronitrile and ethylene diamine in analogy to Example 22: colourless powder;MS (ISP): 223.0 ((M+H)+.).

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

Procedure: rac-2-(3-chloro-phenyl)-butyronitrile was prepared from rac-1-(1-bromo-propyl)-3-chloro-benzene and trimethylsilyl cyanide in analogy to Example 23 c): colourless oil.

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

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

Procedure: A solution of 2-(3-chlorophenyl)butanenitrile (4.69 g, 26 mmol) and MeI (2.0 mL, 31 mmol) in DMSO (15 mL) was added dropwise to a stirred solution of NaH (60% dispersion in mineral oil (1.3 g, 31 mmol)) in DMSO (35 mL) at 0° C. under a nitrogen atmosphere. The reaction mixture was stirred for 30 minutes at 0° C. and then brought to room temperature and stirred for 15 hours. The reaction mixture was quenched with water carefully and then diluted with EtOAc. The organic layer was separated, washed with water (2×) and brine, dried (MgSO4), and concentrated in vacuo to give the desired compound as a light yellow oil (5.54 g). brought to room temperature stirred for 15 hours The reaction mixture was quenched with water carefully diluted with EtOAc The organic layer was separated washed with water (2×) and brine dried (MgSO4) concentrated in vacuo

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

Procedure: A solution of 2-(3-chlorophenyl)acetonitrile (10.00 g, 66 mmol) and ethyl bromide (4.9 mL, 66 mmol) in DMSO (25 mL) was added dropwise to a stirred solution of NaH (60% dispersion in mineral oil (2.6 g, 66 mmol)) in DMSO (75 mL) at 0° C. under a nitrogen atmosphere. The reaction mixture was stirred for 30 minutes at 0° C. and then brought to room temperature and stirred for 23 hours. The reaction mixture was carefully quenched with water, and was then diluted with EtOAc. The organic layer was separated, washed with water (2×) and brine, dried (MgSO4), and concentrated in vacuo to give the crude product as an orange oil. The crude oil was purified by silica flash chromatography (0-5% EtOAc/hexane) to give the desired compound as a colorless oil (4.69 g). brought to room temperature stirred for 23 hours The reaction mixture was carefully quenched with water was then diluted with EtOAc The organic layer was separated washed with water (2×) and brine dried (MgSO4) concentrated in vacuo to give the crude product as an orange oil The crude oil was purified by silica flash chromatography (0-5% EtOAc/hexane)

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

Procedure: A solution of 2-(3-chlorophenyl)butanenitrile (4.69 g, 26 mmol) and MeI (2.0 mL, 31 mmol) in DMSO (15 mL) was added dropwise to a stirred solution of NaH (60% dispersion in mineral oil (1.3 g, 31 mmol)) in DMSO (35 mL) at 0° C. under a nitrogen atmosphere. The reaction mixture was stirred for 30 minutes at 0° C. and then brought to room temperature and stirred for 15 hours. The reaction mixture was quenched with water carefully and then diluted with EtOAc. The organic layer was separated, washed with water (2×) and brine, dried (MgSO4), and concentrated in vacuo to give the desired compound as a light yellow oil (5.54 g). brought to room temperature stirred for 15 hours The reaction mixture was quenched with water carefully diluted with EtOAc The organic layer was separated washed with water (2×) and brine dried (MgSO4) concentrated in vacuo

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

Procedure: A solution of 2-(3-chlorophenyl)acetonitrile (10.00 g, 66 mmol) and ethyl bromide (4.9 mL, 66 mmol) in DMSO (25 mL) was added dropwise to a stirred solution of NaH (60% dispersion in mineral oil (2.6 g, 66 mmol)) in DMSO (75 mL) at 0° C. under a nitrogen atmosphere. The reaction mixture was stirred for 30 minutes at 0° C. and then brought to room temperature and stirred for 23 hours. The reaction mixture was carefully quenched with water, and was then diluted with EtOAc. The organic layer was separated, washed with water (2×) and brine, dried (MgSO4), and concentrated in vacuo to give the crude product as an orange oil. The crude oil was purified by silica flash chromatography (0-5% EtOAc/hexane) to give the desired compound as a colorless oil (4.69 g). brought to room temperature stirred for 23 hours The reaction mixture was carefully quenched with water was then diluted with EtOAc The organic layer was separated washed with water (2×) and brine dried (MgSO4) concentrated in vacuo to give the crude product as an orange oil The crude oil was purified by silica flash chromatography (0-5% EtOAc/hexane)