1-(4-AMINOBENZOYL)-4-METHYLPIPERAZINE

Step: 3A-2Synthesis of (4- Amino-phenyl)-(4-methy 1-piperazin-l - l)-methanone.Procedure:Pd-C (150mg) was added to a solution of (4-Methyl-piperazin-l-yl)-(4-nitro-phenyl)- methanone (440mg, 1.7670mmol) in MeOH and stirred for 2hrs in a hydrogen atmosphere. The reaction was monitored by the TLC (10percent MeOH: CHC1A mixture of 3a (1.20 g, 4.81mmol) and Pd/C (0.102 g, 0.096 mmol) in MeOH (25 mL) was stirred under H2 overnight.The suspension was filtered through a pad of Celite and the pad was washed with EtOH(10 mL×3). The combined filtrates were concentrated and the crude was purified bycolumn chromatography on silica gel (DCM: MeOH =20:1) to give the title compound3b (1.0 g, 95 percent yield). LCMS: 220.1 [M+H]+.Step 2: (4-Amino-phenyl)-(4-methy -piperazine-l-yl)-methanoneTo a solution of (4-Methyl-piperazin-l-yl)-(4-nitro-phenyl)-methanone (14 g, 0.05623 mol) in MeOH (100 mL) was added Pd/C 10percent (1.4 g) in portions and the Parr reaction vessel was purged with nitrogen for 10 min. reaction vessel was fixed in Pan- shaker at 60 psi pressure for 3 h. The reaction mixture was filtered through the Celite.(R). pad and the filtrate was concentrated under reduced pressure to afford the title compound [11 g, 89percent]; LC-MS (ESI): Calculated mass 219.1; Observed mass: 220.1 [M+H]A mixture containing (4-methylpiperazin-1-yl)(4-nitrophenyl)methanone (27) (200 mg, 0.802 mmol) and 10percent Pd/C (60 mg) in 20 mL of Ethanol was shaken under HTo a mixture of 4-aminobenzoic acid (5g, 36.5 mmol), 1-methylpiperazine (3.7 mL, 32.8 mmol) and TEA (16.0 mL, 114.8 mmol) in DCM (100 mL) was added EDC.HCl (10.5 g, 54.8 mmol) and the mixture was stirred at room temperature overnight. The sovent was removed and the residue was purified by silica flash chromatography with 0 to 10percent MeOH in DCM. The light yellow oil obtained was dissolved in DCM and filtered. The yellow solid obtained was dissolved in DCM washed with brine then with Na

Molecular Weight:219.28
XLogP3:-0.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:219.137162174
Monoisotopic Mass:219.137162174
Topological Polar Surface Area:49.6
Heavy Atom Count:16
Complexity:241
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes