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[ CAS No. 138227-62-0 ]

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2D
Chemical Structure| 138227-62-0
Chemical Structure| 138227-62-0
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Product Details of [ 138227-62-0 ]

CAS No. :138227-62-0MDL No. :MFCD06200882
Formula : C16H22N2O5 Boiling Point : 453.7°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :322.36Pubchem ID :-
Synonyms :

Computed Properties of [ 138227-62-0 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 138227-62-0 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 138227-62-0 ]

  • Upstream synthesis route of [ 138227-62-0 ]
  • Downstream synthetic route of [ 138227-62-0 ]

[ 138227-62-0 ] Synthesis Path-Upstream   1~2

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YieldReaction ConditionsOperation in experiment
99% With hydrogen In methanol at 20℃; for 4 h; To a solution of 4-(1-t-butoxycarbonylpiperidin-4-yloxy)nitrobenzene (11.9 g) obtained in reference example 105 in methanol (100 ml) was added palladium on carbon (1.9 g), and the resulting mixture was stirred at room temperature under a hydrogen atmosphere for 4 hours. At the end of this time, the reaction mixture was filtered, and the filtrate was evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (1:1) as the eluent to afford the title compound (10.7 g, yield: 99 percent) as a pale red solid. 1H NMR (400MHz, CDCl3) δ ppm : 1.46 (9H, s), 1.71 (2H, m), 1.87 (2H, m), 3.27 (2H, m), 3.71 (2H, m), 4.26 (1H, m), 6.63 (2H, d, J=8.5), 6.76 (2H, d, J=8.5).
95% With palladium 10% on activated carbon; ammonium formate In methanol at 50℃; Inert atmosphere; Reflux 4.2.8
Tert-Butyl 4-(4-aminophenoxy)piperidine-1-carboxylate (12)
In a round bottom flask equipped with a magnetic stirring bar and under nitrogen atmosphere, product 11 (11.42 g, 35.4 mmol) and ammonium formate (21.5 g, 354 mmol) were dissolved in 210 mL of degassed MeOH and the solution was heated to 50 °C. 10percent w/w Palladium on activated charcoal (1.10 g) was added and the reaction mixture was stirred at 90 °C (oil bath temperature, in order to ensure a round-boiling reflux of the reaction mixture, even after development of water as a coproduct of the hydrogenation) for 5 h.
Hereafter, the reaction mixture was filtered through a short plug of celite, washed with DCM (100 mL) and evaporated in vacuo to give 9.28 g (32.2 mmol, 95percent yield) of pure 12 as a brown solid (m. p. = 80-81 °C).
1H NMR (300 MHz, CDCl3) δ = 6.77-6.71 (m, 2H); 6.63-6.58 (m, 2H); 4.24 (sept, J = 3.6 Hz, 1H); 3.73-3.65 (m, 2H); 3.46 (bs, 2H); 3.29-3.21 (m, 2H); 1.90-1.81 (m, 2H); 1.73-1.62 (m, 2H); 1.45 (s, 9H) ppm. 13C NMR (100 MHz, CDCl3) δ = 154.9; 150.0; 140.7, 118.3; 116.4; 79.5; 73.7; 40.7 (broad); 30.8; 28.4 ppm. IR (KBr) ν = 3460.0, 3361.6, 2955.4, 1685.1, 1509.9, 1419.4, 1229.0, 1049.6 cm-1. GCMS (EI) m/z = 291 [M], 219 [M- iBuO]+, 192 [M- isobutylene - CO2]+ ·, 184 [M- PhNH2, - H2O]+ ·, 128 [M- PhNH2, - H2O - isobutylene]+ ·, 109 [4-aminophenol]+ ·, 84 [M- PhNH2, - H2O - isobutylene - CO2]+ ·.
93% With palladium 10% on activated carbon; hydrogen In methanol at 50℃; A solution of tert—butyl 4—(4—nitrophenoxy)piperidine—1—carboxylate (611 mg, 1.895 mmol) in methanol (60 mL) washydrogenated by H-Cube (10percent Pd/C cartridge, Full H2, 50°C, 1 mL/min) . The reaction mixture was concentrated to dryness under reduced pressure to give the title compound as a pale pink solid (517 mg, 93percent) . ‘H NMR (300 MHz,CDC13) : 3 6.76 (dt, 2H), 6.63 (dt, 2H), 4.26 (sep, 1H),3.71 (ddd, 2H), 3.45 (br s, 2H), 3.26 (ddd, 2H), 1.80—1.95 (m, 2H), 1.61—1.78 (m, 2H), 1.46 (s, 9H) . LCMS(Method C) : = 0.85 mi m/z = 237 [M_tBu+H]+.
82.3% With hydrogen In methanol; ethanol at 22℃; for 2 h; A mixture of 4-(4-nitro-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (3.15 g, 9.77 mmol) and 10percent wt palladium on carbon (1.01 g) in anhydrous ethanol-methanol (1:1, 100 mL) is stirred vigorously under hydrogen gas at 22°C for 2 hr. Then the palladium on carbon is removed by filtration. The filtrate is concentrated to give a white solid (2.35 g, 82.3 percent yield).

Reference: [1] Chemical and Pharmaceutical Bulletin, 2008, vol. 56, # 6, p. 758 - 770
[2] Patent: EP1375482, 2004, A1, . Location in patent: Page 159
[3] Bioorganic and medicinal chemistry, 2002, vol. 10, # 5, p. 1509 - 1523
[4] European Journal of Medicinal Chemistry, 2016, vol. 117, p. 1 - 7
[5] Patent: WO2015/92431, 2015, A1, . Location in patent: Page/Page column 205; 206
[6] Patent: EP1609789, 2005, A1, . Location in patent: Page/Page column 11
[7] Patent: WO2014/26242, 2014, A1, . Location in patent: Page/Page column 153; 154
[8] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 3, p. 561 - 566
[9] Bioorganic and medicinal chemistry letters, 2004, vol. 14, # 16, p. 4281 - 4286
[10] Patent: US6562828, 2003, B1,
[11] Patent: EP976722, 2000, A1,
[12] Patent: EP1020434, 2000, A1,
[13] Patent: US6350761, 2002, B1, . Location in patent: Page column 43
[14] Patent: US2007/167435, 2007, A1, . Location in patent: Page/Page column 20-21
[15] Patent: WO2017/23133, 2017, A2, . Location in patent: Paragraph 4965-4967
[16] Patent: WO2008/141976, 2008, A1, . Location in patent: Page/Page column 227; 228
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Reference: [1] Patent: US6555556, 2003, B1,
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