5-fluoro-2,3-dihydro-1H-inden-1-amine

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: Zinc powder (20.2 g) was added during three hours to the stirred solution of the above oxime (20.2 g) in acetic acid (200 ml) which maintains the temperature at 25°-35° C. The resulting mixture was stirred an additional 12 hours at room temperature. The solids were removed by filtration and the filtrate concentrated in vacuo. The concentrated filtrate was partitioned between water and toluene and the aqueous phase adjusted to pH 12 with ammonium hydroxide and extracted with toluene. Solvent removal in vacuo gave 5-fluoro-1-aminoindan (17.8 g) as a colored oil. at 25°-35° C The solids were removed by filtration the filtrate concentrated in vacuo The concentrated filtrate was partitioned between water and toluene extracted with toluene Solvent removal in vacuo

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: Use a method similar to the General Procedure 5-3 to couple 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (426 mg, 1.0 mmol) with 1-(3-chloro-4-fluoro-phenyl)-ethylamine Isomer 1 (226 mg, 1.3 mmol). Purify by chromatography on silica gel eluting with EtOAc/hexane (1:7) to give 7-chloro-6-[1-(3-chloro-4-fluoro-phenyl)-ethylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow oil (293 mg, 65%). Purify by chromatography on silica gel eluting with EtOAc/hexane (1:7)

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

Procedure: Zinc powder (20.2 g) was added during three hours to the stirred solution of the above oxime (20.2 g) in acetic acid (200 ml) which maintains the temperature at 25°-35° C. The resulting mixture was stirred an additional 12 hours at room temperature. The solids were removed by filtration and the filtrate concentrated in vacuo. The concentrated filtrate was partitioned between water and toluene and the aqueous phase adjusted to pH 12 with ammonium hydroxide and extracted with toluene. Solvent removal in vacuo gave 5-fluoro-1-aminoindan (17.8 g) as a colored oil. at 25°-35° C The solids were removed by filtration the filtrate concentrated in vacuo The concentrated filtrate was partitioned between water and toluene extracted with toluene Solvent removal in vacuo

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

Procedure: Zinc powder (20.2 g) was added during three hours to the stirred solution of the above oxime (20.2 g) in acetic acid (200 ml) which maintains the temperature at 25°-35° C. The resulting mixture was stirred an additional 12 hours at room temperature. The solids were removed by filtration and the filtrate concentrated in vacuo. The concentrated filtrate was partitioned between water and toluene and the aqueous phase adjusted to pH 12 with ammonium hydroxide and extracted with toluene. Solvent removal in vacuo gave 5-fluoro-1-aminoindan (17.8 g) as a colored oil. at 25°-35° C The solids were removed by filtration the filtrate concentrated in vacuo The concentrated filtrate was partitioned between water and toluene extracted with toluene Solvent removal in vacuo

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

Procedure: prepared by reaction of 1-(3,4-Dimethoxy-benzyl)-6-methoxy-7-isopropoxy-1,2,3,4-tetrahydroisoquinoline and 2-bromoacetyl bromide with 1-amino-5-fluoro-indane

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

Procedure: prepared by reaction of 1-(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline and 2-bromoacetyl bromide with 1-amino-5-fluoro-indane

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

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

Procedure: prepared by reaction of 1-(3,4-Dimethoxy-benzyl)-6-methoxy-7-isopropoxy-1,2,3,4-tetrahydroisoquinoline and 2-bromoacetyl bromide with 1-amino-5-fluoro-indane