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Chemical Structure| 158144-85-5 Chemical Structure| 158144-85-5

Structure of 158144-85-5

Chemical Structure| 158144-85-5

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Product Details of [ 158144-85-5 ]

CAS No. :158144-85-5
Formula : C17H25NO3
M.W : 291.39
SMILES Code : O=C(N1CCC(C2=CC=CC=C2)(CO)CC1)OC(C)(C)C
MDL No. :MFCD11044987

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Application In Synthesis of [ 158144-85-5 ]

* 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 [ 158144-85-5 ]

[ 158144-85-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 3913-23-3 ]
  • [ 158144-85-5 ]
  • [ 954123-81-0 ]
YieldReaction ConditionsOperation in experiment
71% With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20℃; for 1.5h; tert-Butyl 4-((2-methoxy-5-nitrobenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate. 2-(Bromomethyl)-1-methoxy-4-nitrobenzene (100.0 mg, 0.34 mmol) and tert-butyl 4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylate (93.0 mg, 0.38 mmol) were combined in dimethylformamide (4 mL) and cooled to 0 C. The reaction was treated with sodium hydride (9.0 mg, 0.38 mmol), stirred at 0 C. for 1 hr and at room temperature for 30 min. The reaction mixture was diluted with water and extracted with ethyl acetate (2×). The organic layers were pooled together, washed with brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (15% ethyl acetate/hexanes) gave 110 mg (71%). 1H-NMR (CDCl3, 500 MHz) delta 8.11 (dd, J=6.1, 3.1 Hz, 1H), 8.08 (d, J=2.8 Hz, 1H), 7.34 (m, 4H), 7.21-7.24 (m, 1H), 6.80 (d, J=8.9 Hz, 1H), 4.37 (s, 2H), 3.85 (s, 3H), 3.74-3.75 (m, 2H), 3.48 (s, 2H), 3.02-3.07 (m, 2H), 2.21-2.24 (m, 2H), 1.87-1.93 (m, 2H), 1.43 (s, 9H). Mass spec.: 479.16 (MNa)+.
  • 2
  • [ 158144-85-5 ]
  • [ 175204-45-2 ]
  • [ 1175065-55-0 ]
YieldReaction ConditionsOperation in experiment
22% EXAMPLE 29 2,6-dichloro-4(((4-phenylpiperidin-4-yl)methoxy)methyl)pyridine. This compound was prepared according to the experimental condition of intermediate 5 from 4-(bromomethyl-2,6-dichloro)pyridine (131 mg, 0.55 mmoL), and and tert-butyl 4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylate (145 mg, 0.50 mmol) to afford 50.0 mg (22%) of the desired compound. The resulting residue was taken directly towards deprotection following the procedure outlined in Example 28 to afford 10 mg (5% overall) of the desired compound as the TFA salt. 1H-NMR (CD3OD,400 MHz) δ7.34-7.48 (m, 5H), 7.10 (s, 2H), 4.43 (s, 2H), 3.49 (s, 2H) 3.29-3.40 (m, 2H), 2.89-2.96 (m, 2H), 2.50-2.56 (m, 2H), 2.15-2.19 (m, 2H). Mass spec.: 351.10 (MH)+. EXAMPLE 30
 

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