N,N-diethylpiperidin-4-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:

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

Procedure: To a solution of 4-(diethylamino)piperidine dihydrochloride (3.0 g, 0.019 mmol) in water (20 mL), 2M sodium hydroxide solution (5.0 mL) was added at ambient temperature. The mixture was stirred for 30 min. The solvent was removed under reduced pressure, and methanol (10 mL) was added to the crude material, then the residue was removed by filtration. The filtrate was concentrated and dried to afford 4-(diethylamino)piperidine (1.7 g, y. 77%) as solid. The solvent was removed under reduced pressure, and methanol (10 mL) was added to the crude material the residue was removed by filtration The filtrate was concentrated dried

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

Procedure: 2-(7-Bromo-4-quinolylamino)benzoic acid is converted to the acid chloride which is reacted with 4-diethylamino piperidine as in Example 1 to give the title compound.

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

Procedure: The title compound is synthesized by coupling of Diethyl-piperidin-4-yl-amine (commercially available from CHESS GmbH) and bromoacetonitrile analogously to the preparation of Intermediate 149.2 as a colorless oil; ES-MS: M+=196.2: 1HNMR(DMSO-d6) 3.65 (s, 2H), 2.80-2.75 (m, 2H), 2.45-2.30 (m, 5H), 2.15-2.05 (m, 2H), 1.70-1.60 (m, 2H), 1.45-1.35 (m, 2H), 0.95 (t, 6H). analogously to the preparation of Intermediate 149.2 as a colorless oil

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

Procedure: To a solution of 4-(diethylamino)piperidine dihydrochloride (3.0 g, 0.019 mmol) in water (20 mL), 2M sodium hydroxide solution (5.0 mL) was added at ambient temperature. The mixture was stirred for 30 min. The solvent was removed under reduced pressure, and methanol (10 mL) was added to the crude material, then the residue was removed by filtration. The filtrate was concentrated and dried to afford 4-(diethylamino)piperidine (1.7 g, y. 77%) as solid. The solvent was removed under reduced pressure, and methanol (10 mL) was added to the crude material the residue was removed by filtration The filtrate was concentrated dried

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: In a manner analogous to the method described in examples 8, (4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride (example 51) was coupled with diethyl-4-piperidinylamine (Astatech) to give the title compound. HR-MS (ES, m/z) calculated for C38H50Cl2N5O2 [(M+H)+] 678.3336, observed 678.3335.

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

Procedure: 2.1 g (13.25 mmol) of 4-(N,N-diethylamino)piperidine, 1.8 g (13.25 mmol) of 4-fluoroacetophenone and 7.3 g of potassium carbonate in 100 ml of dimethylformamide/n-propanol (1:1) were refluxed for 20 h. 1.9 g of 1-(4-acetylphenyl)-4-(N,N-diethylamino)piperidine were obtained as crystalline fumarate. Melting point 125°-127° C.

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

Procedure: The same procedures as in Example 2 were carried out using (E)-2-decenoic acid and 4-diethylaminopiperidine as starting raw materials, to produce an intended compound. to produce an intended compound