1-(2,6-dimethylphenyl)piperazine

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

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

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

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: 4-(2,6-Dimethylphenyl) piperazine (1 g, 5.23 mmol) in MeOH (10 ml) was cooled to 0° and 0.305 g (5.73 mmol) of acrilonitrile was added. The reaction was stirred overnight at room temperature and evaporated under vacuum affording 1 g of crude 3-[4-(2,6-dimethylphenyl)piperazin-1-yl]propionitrile as a waxy solid. This compound was dissolved in MeOH (60 ml), 2 ml 37% HCl and hydrogenated under pressure (40 psi) with 0.2 g of 10% Pd\C. The reaction was filtered and evaporated to dryness obtaining 1 g of the title compound, as a hydrochloride salt, that was used without further purification for the following reaction. evaporated under vacuum

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

Procedure: The title compound was prepared in similar fashion from (S)-(+)-4-(oxiranylmethoxy)-1H-indole and 1-(2,6-dimethylphenyl)piperazine. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 50% overall yield. FDMS m/e=379 (M+ of free base). α[D]589 =-11.89 (c=0.47, methanol).

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

Procedure: The title compound was prepared in similar fashion from (S)-(+)-4-(oxiranylmethoxy)-1H-indole and 1-(2,6-dimethylphenyl)piperazine. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 50% overall yield. FDMS m/e=379 (M+ of free base). α[D]589=−11.89 (c=0.47, methanol).

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

Procedure: The title compound was prepared in similar fashion from (S)-(+)-4-(oxiranylmethoxy)-1H-indole and 1-(2,6-dimethylphenyl)piperazine. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 50% overall yield. FDMS m/e=379 (M+ of free base). α[D]589 =-11.89 (c=0.47, methanol).

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

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

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