1-ACETYL-4-METHYLPIPERAZINE HYDROCHLORIDE

A solution of /V-methylpiperazine (2.0 g, 19.97 mmol), triethylamine (3.35 mL, 23.96 mmol) and acetic anhydride (2.3 mL, 23.96 mmol) in EtOH (60 mL) was stirred at room temperature overnight. The reaction mixture was evaporated to dryness. Purification of the residue by silica gel column chromatography (CHa) Synthesis of 1-(4-methylpiperazin-1-yl)ethanone A solution of N-methylpiperazine (2.0 g, 19.97 mmol), triethylamine (3.35 mL, 23.96 mmol) and acetic anhydride (2.3 mL, 23.96 mmol) in EtOH (60 mL) was stirred at room temperature overnight. The reaction mixture was evaporated to dryness. Purification of the residue by silica gel column chromatography (CHGeneral procedure: In a glass reaction vessel, 2 mmol of 2- (benzylamino) ethanol, 45 mg of catalyst D, 20 mL of dehydrated methanol, and a magnetic stirrer.Then, an argon gas was introduced into the sealed reaction system, and under a condition of 25 C., While stirring the reaction system, ultraviolet rays were irradiated for 10 hours.When the reaction solution was subjected to GC-MS analysis, Only 2- (N-methylbenzylamino) ethanol was obtained(Yield 87%, see Table 3).General procedure: Amine (1.0mmol) was added to phenylmethylene diacetate 3 (0.291g, 1.5mmol) and the reaction stirred at 70C for 16h. The crude reaction product was then purified by silica gel chromatography to give the desired acetamide. In those cases, where the reaction mixture was not homogeneous, then 2mL of EtOAc or toluene were added as cosolvent at the start of the reaction.A solution of /V-methylpiperazine (2.0 g, 19.97 mmol), triethylamine (3.35 mL, 23.96 mmol) and acetic anhydride (2.3 mL, 23.96 mmol) in EtOH (60 mL) was stirred at room temperature overnight. The reaction mixture was evaporated to dryness. Purification of the residue by silica gel column chromatography (CH2CI2: MeOH mixtures of increasing polarity as eluent) afforded the desired product (2.16 g, 76%) as a yellow oil. 1 H-NMR (CDCI3, 300 MHz) delta: 3.65 (t, J= 6.8 Hz, 2H), 3.49 (t, J= 6.8 Hz, 2H), 2.46- 2.39 (m, 4H), 2.32 (s, 3H), 2.10 (s, 3H) ppm.a) Synthesis of To a solution of 1 -(4-methylpiperazin-1 -yl)ethanone (1 .68 g, 1 1 .8 mmol) in THF (25 mL) cooled to -78 C, a solution of LDA (1 .5 M in THF, 9.8 mL, 14.75 mmol) was added, and the resulting mixture was stirred at -78 ^ for 1 h under argon atmosphere. Finally, a solution of 4-bromoindan-1 -one (1 .25 g, 5.9 mmol) in THF (50 mL) was added, and the resulting mixture was kept at -78 ' for 4 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic extracts were dried over Na2S04 and evaporated to dryness. A solution of the previous residue in AcOH:H2S04:H20 (79 mL, 85:10:5) was stirred for 6 h. The reaction mixture was poured into water, basified with 50% NaOH and extracted with EtOAc. The organic extract, after being dried over Na2S04, was evaporated to dryness. To a solution of the previous residue in THF (75 mL) cooled to 0 C, AIH3- NMe2Et (0.5 M in toluene, 20 mL, 10.34 mmol) was added and the resulting mixture was stirred for 5 h. EtOAc:H20 (90 mL, 1 :1 ) was added to the reaction mixture and the resulting suspension was filtered through Celite. The layers were separated and the aqueous phase was extracted with EtOAc. The organic extract was dried over Na2S04 and evaporated to dryness. A solution of the previous residue in 37% HCLEtOH (150 mL, 1 :1 ) was refluxed overnight. The reaction mixture was evaporated to dryness. Purification of the residue by silica gel column chromatography (EtOAc/NH3:MeOH mixtures of increasing polarity as eluent) afforded the desired product (981 mg, 51 %). 1 H-NMR (CDCI3, 300 MHz) delta: 7.32 (m, 2H), 7.18 (t, J= 7.6 Hz, 1 H), 6.30 (s, 1 H), 3.31 (d, J= 1 .8 Hz, 2H), 2.72 (m, 4H), 2.60 (m, 4H), 2.51 (m, 4H), 2.30 (s, 3H) ppm. EI-MS m/z: 320.1 (M).b) Synthesis of 1-(2-(7-bromo-1H-inden-3-yl)ethyl)-4-methylpiperazine To a solution of

Molecular Weight:142.20
XLogP3:-0.5
Hydrogen Bond Acceptor Count:2
Exact Mass:142.110613074
Monoisotopic Mass:142.110613074
Topological Polar Surface Area:23.6
Heavy Atom Count:10
Complexity:128
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes