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[ CAS No. 350684-49-0 ]

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Chemical Structure| 350684-49-0
Chemical Structure| 350684-49-0
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Product Details of [ 350684-49-0 ]

CAS No. :350684-49-0 MDL No. :MFCD06659531
Formula : C16H23N3O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :305.37 g/mol Pubchem ID :2763355
Synonyms :

Safety of [ 350684-49-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 350684-49-0 ]

  • Upstream synthesis route of [ 350684-49-0 ]
  • Downstream synthetic route of [ 350684-49-0 ]

[ 350684-49-0 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 509073-62-5 ]
  • [ 350684-49-0 ]
YieldReaction ConditionsOperation in experiment
100% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 18 h; [0260j A mixture of tert-butyl 4-(4-nitrobenzoyl)piperazine- 1 -carboxylate (20 g, 60 mmol) and 10percent Pd/C (4 g) in MeOH (600 mL) was stirred under 1 atmosphere of H2 at room temperature for for 18 h. The solution was filtered through Celite and the filtrate was concentrated under reduced pressure to afford 18 g of tert-butyl 4-(4- aminobenzoyl)piperazine-1-carboxylate as a white solid (100percent).
98% With palladium 10% on activated carbon; hydrogen In methanol for 12 h; A solution of tert-butyl 4-(4-nitrobenzoyl)piperazine-1-carboxylate (4) (335 mg, 1 mmol) in 30 mL of anhydrous methanol wasadded 10percent Pd / percent (W / w), 34 mg) hydrogenation catalyst. Vacuum, pour hydrogen, stir the reaction overnight. 12After theaddition of Pd / C, the solvent was removed by evaporation under reduced pressure to give a white solid which was subjectedto the next reaction without purification.
98% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 3 h; To a degassed solution of tert-butyl 4-(4-nitrobenzoyl)piperazine-1-carboxylate (2c, 4.1 g, 12.3 mmol, 1 equiv.) in anhydrous MeOH (40 mL) was added Pd/C (10percent wt., dry; 600 mg).The reaction was sealed, fifted with a H2 balloon and then stirred for 3 h at room temperature. The reaction mixture was filtered through Celite and then concentrated to obtain the product 2d as a white foam (3.7 g, 12 mmol, 98percent yield).
98% With palladium 10% on activated carbon; hydrogen In methanol; water at 20℃; for 3 h; Sealed tube To a degassed solution of tert-butyl 4-(4-nitrobenzoyl)piperazine-1-carboxylate (2c, 4.1 g, 12.3 mmol, 1 equiv.) in anhydrous MeOH (40 mL) was added Pd/C (10percent wt., dry; 600 mg). The reaction was sealed, fitted with a H2 balloon and then stirred for 3 h at room temperature. The reaction mixture was filtered through Celite and then concentrated to obtain the product 2d as a white foam (3.7 g, 12 mmol, 98percent yield).
93% With hydrogen In methanol at 20℃; Step b - terf-butyl 4-(4-aminobenzoyl)piperazine-1-carboxylate; <n="163"/>A solution of tert-butyl 4-(4-nitrobenzoyl)piperazine-1-carboxylate (1.0Og, 3.00mmol) in MeOH (60ml) was hydrogenated at 2O0C at atmospheric pressure using an H-Cube (flow rate at 1 ml/min and full hydrogen mode) using a Pd/C cartridge. The solvent was removed in vacuo Xo afford te/f-butyl 4-(4-aminobenzoyl)piperazine-1-carboxylate (0.85g, 2.79mmol, 93percent) as a white solid. 1H NMR (CDCI3) δ 1.41 (9H, s), 3.38 (4H, m), 3.53 (4H, m), 4.07 (2H, br. s), 6.55 (2H, d), 7.17 (2H, d). LCMS (2) Rt: 2.14min; m/z (ES+) 306.

Reference: [1] Patent: WO2013/177536, 2013, A2, . Location in patent: Paragraph 0260
[2] Patent: CN102464631, 2016, B, . Location in patent: Paragraph 0094-0096
[3] Patent: WO2018/98275, 2018, A1, . Location in patent: Page/Page column 126
[4] Patent: WO2018/98288, 2018, A1, . Location in patent: Page/Page column 154; 155
[5] Patent: WO2008/139161, 2008, A1, . Location in patent: Page/Page column 161-162
[6] Patent: WO2010/80474, 2010, A1, . Location in patent: Page/Page column 141
  • 2
  • [ 150-13-0 ]
  • [ 57260-71-6 ]
  • [ 350684-49-0 ]
YieldReaction ConditionsOperation in experiment
87% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; butan-1-ol In DMF (N,N-dimethyl-formamide) at 20℃; for 22 h; To a solution of 4-aminobenzoic acid (411 mg, 3.00 mmol) in DMF (3.0 mL) at room temperature was added EDC (862 mg, 4.50 mmol), HOBt (608 mg, 4.50 mmol), triethylamine (606 mg, 0.835 mL, 6.00 mmol) and tert-butyl piperazinecarboxylate (671 mg, 3.60 mmol). The mixture was stirred for 22 h, and then 2 N aq. NaOH was added to adjust the PH>10. The mixture was extracted with ethyl acetate, and the organic layer was dried over MgSO4, concentrated. The residue was purified by silica gel column chromatograghy eluted with EtOAc:hexanes (50 to 90percent EtOAc) to give 4-(4-amino-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester (796 mg, 87percent) as a colorless oil. MS (ES+): m/z = 306.2
Reference: [1] Patent: WO2004/46120, 2004, A2, . Location in patent: Page 179
[2] Patent: WO2014/26242, 2014, A1, . Location in patent: Page/Page column 95
[3] Patent: WO2009/138438, 2009, A1, . Location in patent: Page/Page column 26
  • 3
  • [ 57260-71-6 ]
  • [ 62-23-7 ]
  • [ 350684-49-0 ]
Reference: [1] Patent: WO2013/177536, 2013, A2,
[2] Patent: WO2008/139161, 2008, A1,
  • 4
  • [ 57260-71-6 ]
  • [ 350684-49-0 ]
Reference: [1] Patent: WO2018/98275, 2018, A1,
[2] Patent: WO2018/98288, 2018, A1,
  • 5
  • [ 62-23-7 ]
  • [ 350684-49-0 ]
Reference: [1] Patent: WO2018/98275, 2018, A1,
[2] Patent: WO2018/98288, 2018, A1,
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