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Chemical Structure| 92086-93-6 Chemical Structure| 92086-93-6

Structure of 92086-93-6

Chemical Structure| 92086-93-6

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Product Details of [ 92086-93-6 ]

CAS No. :92086-93-6
Formula : C12H16ClNO2
M.W : 241.71
SMILES Code : O=C(C1N(CC2=CC=CC=C2)CCC1)O.[H]Cl
MDL No. :MFCD00157011

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Application In Synthesis of [ 92086-93-6 ]

* 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 [ 92086-93-6 ]

[ 92086-93-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 92086-93-6 ]
  • [ 2835-77-0 ]
  • [ 96293-17-3 ]
YieldReaction ConditionsOperation in experiment
86% To a round bottomed flask containing dry DCM (475 mL) under N2 was added 7 (34.5 g, 143 mmol, 1 equiv.) to form a cloudy suspension. The reaction mixture was cooled to -20 C using a mixture of ice and NaCl (1:3), giving (on average) an internal temperature of -5 C. N-Methyl imidazole (31.8 mL, 399 mmol, 2.8 equiv.) was then added and stirred for 5 min. Methanesulfonyl chloride (12.2 mL, 157 mmol, 1.1 equiv.) was then added slowly over 5 min, maintaining the internal temperature at between -5 C to 0 C. The reaction mixture was then left to stir at -5 C-0 C for 30 min 2-Aminobenzophenone (25.3 g, 128 mmol, 0.9 equiv.) was then added and the reaction mixture left to stir at room temperature for 17 h. The reaction mixture was quenched with sat. NH4Cl and separated with DCM (3 400 mL). The organic layers were combined, dried and concentrated in vacuo to give the crude as a dark brown oil. The crude was then purified by silica chromatography (0-100% EtOAc in Pet. Ether 40/60) to give the title compound as a yellow solid (42.3 g, 86%). numax (neat): 3248, 2968, 2839, 2810, 1687, 1643, 1576, 1510, 1442 cm-1. 1H NMR (400 MHz, CDCl3): delta 11.54 (s, 1H), 8.59 (dd, 1H, J = 7.6, 1.2 Hz), 7.82-7.80 (m, 2H), 7.67-7.61 (m, 1H), 7.57-7.45 (m, 4H), 7.41-7.39 (m, 2H), 7.18-7.15 (m, 3H), 7.13-7.09 (m, 1H), 3.95 (d, 1H, J = 13.2 Hz), 3.62 (d, 1H, J = 13.2 Hz), 3.37 (dd, 1H, J = 5.2, 4.8 Hz), 3.27-3.22 (m, 1H), 2.47-2.40 (m, 1H), 2.33-2.23 (m, 1H), 2.03-1.96 (m, 1H), 1.90-1.76 (m, 2H). 13C NMR (101 MHz, CDCl3): delta 197.5, 174.1, 138.7, 138.1, 137.7, 132.9, 132.1, 132.0, 129.6, 128.7, 127.8, 127.7, 126.6, 124.9, 121.7, 121.1, 67.8, 59.4, 53.4, 30.5, 23.7. HRMS: (C25H25O2N2) [M+H]+ requires 385.1911, found [M+H]+ 385.1908. [alpha]D20 = -106.7 (c = 1, MeOH). ee = >98% by chiral HPLC, retention time = 11.95 min.
 

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