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Chemical Structure| 25519-80-6 Chemical Structure| 25519-80-6
Chemical Structure| 25519-80-6

Phenyl(piperidin-4-yl)methanone hydrochloride

CAS No.: 25519-80-6

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Cat. No.: A380246 Purity: 98%

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Product Details of [ 25519-80-6 ]

CAS No. :25519-80-6
Formula : C12H16ClNO
M.W : 225.72
SMILES Code : O=C(C1=CC=CC=C1)C2CCNCC2.[H]Cl
MDL No. :MFCD00066982
InChI Key :NXYKIFZJQXOUJS-UHFFFAOYSA-N
Pubchem ID :2724437

Safety of [ 25519-80-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 25519-80-6 ]

* 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 [ 25519-80-6 ]

[ 25519-80-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 24424-99-5 ]
  • [ 25519-80-6 ]
  • [ 193217-39-9 ]
YieldReaction ConditionsOperation in experiment
98% With potassium hydrogencarbonate; In H2 O-TBF; I. Preparation of 4-benzoyl-N-t-butoxylcarbonylpiperidine (compound 86) A mixture of 4-benzoylpiperidine hydrochloride (6.77 g, 30.0 mmol), di-tert-butyldicarbonate (7.2 g, 33.0 mmol) and KHCO3 (6.0 g, 60 mmol) in H2 O--TBF (50/20 mL) was refluxed for 1 h. The reaction mixture was extracted with ethyl acetate (2*100 mL). The combined organic layers were washed with brine, dried over MgSO4. Removal of solvents gave 4-benzoyl-N-t-butoxylcarbonyl-piperidine (8.54 g, 98%); δH (400 MHz, CDCl3) 1.47 (s, 9H), 1.70 (m, 2H), 1.83 (m, 2H), 2.91 (m, 2H), 3.42 (m, 2H), 4.18 (brs, 2H), 7.46 (m, 2H), 7.56 (m, 1H), 7.93 (m, 2H).
94% With triethylamine; In acetonitrile; at 25℃; for 16h; Synthesis of tert-butyl 4-benzoylpiperidi -carboxylate4-Benzoylpiperidine · HC1 (400 mg, 1.78 mmol) was dissolved in acetonitrile (8 mL).Triethylamine (1.25 mL, 8.9 mmol) and di-tert-butyl dicarbonate (465 mg, 2.13 mmol) was added and the reaction was stirred at 25 C for 16 hours. Concentrated reaction mixture under reduced pressure and partitioned between EtOAc (40 mL) and 0.5 M HC1 (20 mL). Discarded aqueous layer and then washed with saturated aqueous sodium bicarbonate (20 mL) followed by brine (20 mL). Dried with MgSC and then under reduced pressure to give the title compound; white solid (484 mg, 94%) NMR (400 MHz, CHLOROFORM-d) δ ppm 7.94 (d, 7=7.53 Hz, 2 H), 7.58 (t, 7=7.00 Hz, 1 H), 7.48 (t, 7=7.50 Hz, 2 H), 4.17 (br. s, 2 H), 3.35 - 3.47 (m, 1 H), 2.79 - 2.99 (m, 2 H), 1.78 - 1.91 (m, 2 H), 1.65 - 1.78 (m, 2 H), 1.47 (s, 9 H)
66% With dmap; triethylamine; In tetrahydrofuran; at 20℃; for 3h; To a mixture of 4-benzoylpiperidine hydrochloride (8, 4.0 g, 17.72 mmol) in THF (48 mL) were added di-tert-butyl dicarbonate (5.2 g, 24.81 mmol), triethylamine (7.4 mL, 53.16 mmol), and 4-dimethylaminopyridine (649 mg, 5.32 mmol) and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, THF was concentrated and EtOAc and water were added. It was extracted with EtOAc and the organic phase was collected, dried over MgSO4, filtered and concentrated. Silica gel column chromatography (EA:HX = 1:5) was done to get 9-2 (3.29 g, 66%- 3 -yield) as a white solid. 1H NMR (CDCl3) δ 7.97-7.90 (m, 2H), 7.51 (ddd, J = 14.8, 7.7, 6.4 Hz, 3H), 4.16 (d, J = 13.3 Hz, 2H), 3.40 (ddd, J = 11.0, 7.4, 3.9 Hz, 1H), 2.98-2.82 (m, 2H), 1.91-1.59 (m, 4H), 1.47 (s, 9H).
5 g With triethylamine; In dichloromethane; at 20℃; for 4h; Step 1:5 To a stirred solution of 4-benzoylpiperidinium chloride (5 g) in dry DCM (50 mL),triethylamine (11 mL) and Boc anhydride (6.7 g) were added. The reaction mixture wasstirred at room temperature for 4 hours and diluted with water (50 mL ). The aqueousphase was extracted with dichloromethane (2 x 25 mL ). The combined organic layer waswashed with brine ( 5 OmL) and dried over anhydrous N a2S04. Evaporation of solvents10 under reduced pressure gave crude product, which was treated with hexane to obtainsolid. The solid obtained was filtered, washed with cold hexane (50 mL) and dried undervacuum to get tert-butyl4-benzoylpiperidine-1-carboxylate (5 g) as white solid. 1H NMR(CDCh): o 1.51 (s, 9H), 1.67-1.76 (m, 2H), 1.85-1.88 (m, 2H), 2.87-2.94 (m, 2H), 3.39-3.45 (m, 1H), 4.16-4.19 (m, 1H), 7.47-7.60 (m, 3H), 7.94-7.96 (m, 2H).

  • 2
  • [ 193217-39-9 ]
  • [ 25519-80-6 ]
YieldReaction ConditionsOperation in experiment
98% With hydrogenchloride; In 1,4-dioxane; at 18 - 25℃; for 0.5h; To this oil was added HCl (2.59 mL, 10.4 ϖαnol, 4M in dioxane) and the solution was stirred for 30 minutes at room temperature. The solvent was removed in vacuo to give phenyl (piperidin-4-yl)methanone hydrochloride (0.023 g, 98%) as a solid: 1H NMR (400 MHz, DMSO- d6) δ 1.75 (m, 2H), 1.95 (m, 2H), 3.04 (m, 2H), 3.48 (m, 2H), 3.69 (m, 2H), 3.77 (m, IH), 7.56 (m, 2H), 7.68 (m, IH), 8.00 (m, 2H) .
 

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