N,N-dimethyl-1-piperidin-2-ylmethanamine

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:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1(e)) (88.3 mg, 0.36 mmol) and N-(2-piperidylmethyl)-dimethylamine (Salor Chemical Company) (0.25 g, 1.72 mmol) was added a solution of K2CO3 (0.25 g, 1.60 mmol) in H2O (2.5 mL). This mixture was stirred at 140° C. in a closed-capped Wheaton vial for 2.5 h. After cooling, CH2Cl2 (10 ML) and H2O (10 mL) were added. The organic solution was removed and the aqueous solution was washed with CH2Cl2 (10 mL). The combined organic solutions were washed with saturated NaCl (15 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (3% MeOH:CHCl3 on silica gel) to give 43 mg (34%) of the title compound as a yellow oil. MS m/z: 350 (M+1), 305, 214. 1H NMR (DMSO-d6; 400 MHz): δ 1.63 (m, 6), 2.29 (s, 6), 2.40 (s, 3), 2.81 (m, 2), 3.03 (br t, 1, J=11.8), 4.53-4.63 (m, 2), 6.75 (s, 1), 7.37 (m, 1), 7.50 (t, 2, J=7.5), 7.81 (d, 2, J=7.8), 12.47 (s, 1). After cooling The organic solution was removed the aqueous solution was washed with CH2Cl2 (10 mL) The combined organic solutions were washed with saturated NaCl (15 mL) dried over MgSO4 filtered concentrated under reduced pressure The residue was purified by flash chromatography (3% MeOH:CHCl3 on silica gel)

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

Procedure: The title compound is prepared analogously to Example 52(a) from racemic 2-[(dimethylamino)methyl]piperidine and D-(-)-tartaric acid. The ditartrate melted at 191°-192.5° C. The base, with a boiling point 17 mm Hg 88°-94° C., had a content of (+)-enantiomer determined by reaction with (S)-(-)-1-phenylethylisocyanate and subsequent HPLC investigation, of 98.5%. [α]D20 =+64° (ethanol). with a boiling point 17 mm Hg 88°-94° C.

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

Procedure: The title compound is prepared analogously to Example 2 from 4-(chloroacetyl)-4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one and 2-[(dimethylamino)methyl]piperidine to give colorless crystals, Mp. 208°-209° C. (acetonitrile/activated charcoal).

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

Procedure: The title compound is prepared analogously to Example 2 from 4-(chloroacetyl)-4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one and 2-[(dimethylamino)methyl]piperidine to give colorless crystals, Mp. 208°-209° C. (acetonitrile/activated charcoal).

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: A solution of 3.5 g. (14.6 mmoles) of 9-acetoxyxanthene and 2.1 g. (14.8 mmoles) of 2-(dimethylaminomethyl)-piperidine in 50 ml. of toluene was refluxed for 40 hours. The mixture was then washed with sodium bicarbonate, dried and evaporated. Recrystallization of the residue from hexane afforded 1-(9-xanthenyl)-2-(dimethylaminomethyl)-piperidine, m.p. 81°-83°C. The mixture was then washed with sodium bicarbonate dried evaporated Recrystallization of the residue from hexane