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Chemical Structure| 1161364-24-4 Chemical Structure| 1161364-24-4

Structure of 1161364-24-4

Chemical Structure| 1161364-24-4

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Product Details of [ 1161364-24-4 ]

CAS No. :1161364-24-4
Formula : C15H20N2O3
M.W : 276.33
SMILES Code : O=C(N1CC(C(NC)=O)CCC1)OCC2=CC=CC=C2

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Application In Synthesis of [ 1161364-24-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1161364-24-4 ]

[ 1161364-24-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 78190-11-1 ]
  • [ 74-89-5 ]
  • [ 1161364-24-4 ]
YieldReaction ConditionsOperation in experiment
61% With dmap; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 48h; Preparation of Intermediates 7, 8, and 9Step 1A mixture of an appropriate amine or (1.0 mmol), N-(benzyloxycarbonyl)nipecotic acid (1.0 mmol), HBTU (1.0 mmol), a catalytic amount of 4-dimethylaminopyridine (DMAP), iV-ethyl- diisopropylethylamine (1.25 mmol), and dry dichloromethane (2 mL) was stirred at room temperature for two days. The solvent was removed under reduced pressure. EtOAc (25 mL) was added and the organic phase was washed with 5 % aqueous citric acid, saturated aqueous <n="67"/>NaHCO3 solution, and brine. After drying (MgSO4), the solvent was removed under reduced pressure. The desired Z-protected nipecotamide derivative was purified by preparative TLC, flash chromatography, or preparative HPLC.Methylamine and ethylamine were applied as 2 M solutions in THF. N-(Benzyloxycarbonyl)- nipecotic acid was commercially available.Benzyl S-Cmethylcarbamoy^piperidine-l-carboxylate: Yield 61 %. 1H NMR (CDCl3, 300 MHz): delta = 1.34-1.53 (m, 1 H), 1.57-1.94 (m, 3 H), 2.25 (m, 1 H, -COCH[CH2J2), 2.73 (d, J= 4.8 Hz, 3 H, -NHCH3), 3.00 (m, 1 H), 3.16 (m, 1 H), 3.91 (m, 1 H), 4.03 (m, 1 H), 5.09 (d, J= 12.5 Hz, 1 H, =NCH2CO), 5.14 (d, J = 12.5 Hz, 1 H, =NCH2CO-), 6.03 (s, br., 1 H, NH), 7.24-7.39 (m, 5 H, Ph). Piperidine ring proton signals were broad and not well resolved.Benzyl 3-(ethylcarbamoyl)piperidine-l-carboxylate: Yield 54 %. 1H NMR (CDCl3, 300 MHz): delta = 1.07 (t, J= 7.2 Hz, 3 H, -CH2CH3), 1.34-1.52 (m, 1 H), 1.57-1.93 (m, 3 H), 2.22 (m, 1 H, -COCH[CH2J2), 3.00 (m, 1 H), 3.16 (m, 1 H), 3.21 (q, J = 7.2 Hz, 1 H, -CH2CH3), 3.23 (q, J= 7.2 Hz, 1 H, -CH2CH3), 3.89 (m, 1 H), 4.02 (m, 1 H), 5.09 (d, br., J= 12.5 Hz, 1 H, =NCH2CO), 5.13 (d, br., J= 12.5 Hz, 1 H, =NCH2CO-), 6.01 (s, br., 1 H, NH), 7.24-7.39 (m, 5 H, Ph). Piperidine ring proton signals were broad and not well resolved.Benzyl 3-(pyrrolidine-l-carbonyl)piperidine-l-carboxylate: Yield 60 %. 1H NMR (CDCl3, 300 MHz): delta = 1.37-1.58 (m, 1 H), 1.64-2.02 (m, 7 H), 2.49 (m, 1 H, -COCH[CH2J2), 2.79 (m, 1 H), 2.95 (m, 1 H), 3.28-3.66 (m, 4 H), 4.20 (m, 2 H), 5.11 (d, J = 12.3 Hz, 1 H, <n="68"/>=NCH2CO), 5.15 (d, J= 12.3 Hz, 1 H, =NCH2CO-), 7.27-7.41 (m, 5 H, Ph). Piperidine ring proton signals were broad and not well resolved.
 

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