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Chemical Structure| 6457-48-3 Chemical Structure| 6457-48-3

Structure of 6457-48-3

Chemical Structure| 6457-48-3

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Product Details of [ 6457-48-3 ]

CAS No. :6457-48-3
Formula : C7H15NO
M.W : 129.20
SMILES Code : CC(O)C1CCNCC1
MDL No. :MFCD00120611

Safety of [ 6457-48-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P301+P330+P331-P302+P352-P305+P351+P338-P304+P340-P310
Class:8
UN#:3259
Packing Group:

Application In Synthesis of [ 6457-48-3 ]

* 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 [ 6457-48-3 ]

[ 6457-48-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 6457-48-3 ]
  • [ 24424-99-5 ]
  • [ 183170-69-6 ]
YieldReaction ConditionsOperation in experiment
93% With triethylamine; In 1,2-dichloro-ethane; at 20℃;Reflux; (+/-)-1-(4-Piperidinyl)ethanol (see reference: WO 9725992A, 12.44 g, 65.7 mmol) in 1,2-dichloroethane (500 mL) was stirred at room temperature and BOC2O (14.36 g, 65.8 mmol) was added followed by Et3N (19 mL, 136 mmol). The stirred mixture was heated at gentle reflux for 15 min and then allowed to cool to room temperature and stirred overnight. The solution was washed twice with 10% citric acid, once with 10% Na2CO3, dried over MgSO4, filtered and concentrated to afford (+/-)-1,1-dimethylethyl 4-(1-hydroxyethyl)-1-piperidinecarboxylate (14 g, 93% yield) as a light amber oil. 1H NMR (400 MHz, DMSO-d6): δ 4.35 (d, 1H, J=4.8 Hz), 3.92 (m, 2H), 3.32 (m, 1H), 2.59 (m, 2H), 1.68 (m, 1H), 1.47 (m, 1H), 1.34 (s, 9H), 1.25 (m, 1H), 1.08-0.88 (m, 2H), 0.97 (d, 3H, J=6.4 Hz).
With sodium hydroxide; In tetrahydrofuran; EXAMPLE 18 1-t-Butyloxycarbonyl-4-hydroxyethylpiperidine A solution of di-t-butyl dicarbonate (10.15 g, 47 mmol) in tetrahydrofuran (15 mL) was added slowly to a 0 C. solution of 4-hydroxyethylpiperidine (5.0 g, 39 mmol) and sodium hydroxide (1.86 g, 47 mmol) in THF. After stirring for 24 hours at room temperature, the mixture was poured into water (200 mL) and extracted with ethyl acetate (3*200 mL). The solution was dried (MgSO4), filtered, and concentrated under vacuum to yield a colorless oil (9.0 g, quant.). 1 H NMR (300 MHz, CDCl3 /TMS, δ): 4.1(m,2H), 3.7(q,2H,J=5Hz), 2.7(br t,2H), 1.7(m,2H), 1.43(s,9H), 1.12-1.00(m,3H) MSCI: 230(MH+, base).
With sodium hydrogencarbonate; In 1,4-dioxane; water; at 0 - 20℃; for 18h;Inert atmosphere; Di-tert-butyl dicarbonate (1.858 g, 8.51 mmol) was added dropwise to a solution of sodium bicarbonate (0.715 g, 8.51 mmol) and l-(piperidin-4-yl)ethan-l-ol (1 g, 7.74 mmol) in Water (10 mL) and 1,4-Dioxane (10 mL) at 0 C under an atmosphere of nitrogen. The reaction was allowed to warm to room temperature and stirred for 18 h. The reaction mixture was diluted with water (100 mL) and extracted with DCM (100 mL). The aqueous layer was extracted with further DCM (3 x 50mL) and the combined organic extracts were dried by passing through a hydrohpbic frit. The solvent was removed under reduced pressure to afford the crude title compound (1.87 g). The material was used directly in the next step.
  • 2
  • [ 183170-69-6 ]
  • [ 6457-48-3 ]
YieldReaction ConditionsOperation in experiment
88.7% To 0.390 g (1.70 mmol) of the above ester is added 5.0 mL (5.0 mmol) of hydrogen chloride as a 1.0 M solution in diethyl ether followed by several drops of methanol to generate a homogeneous mixture. To resulting mixture is stirred at room temperature for 2 hours then an excess of sodium hydroxide is added to make the pH alkaline. The mixture is extracted with ethyl acetate and the combined organic phase is dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide 0.200 g (88.7%) of l-piperidin-4-yl-ethanol as a light yellow oil
 

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