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[ CAS No. 387827-19-2 ]

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2D
Chemical Structure| 387827-19-2
Chemical Structure| 387827-19-2
Structure of 387827-19-2 *Storage: {[proInfo.prStorage]}

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Product Details of [ 387827-19-2 ]

CAS No. :387827-19-2MDL No. :MFCD03701248
Formula : C16H24N2O2 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :276.37Pubchem ID :22049268
Synonyms :

Computed Properties of [ 387827-19-2 ]

TPSA : 55.6 H-Bond Acceptor Count : 3
XLogP3 : 2.7 H-Bond Donor Count : 1
SP3 : 0.56 Rotatable Bond Count : 3

Safety of [ 387827-19-2 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 387827-19-2 ]

  • Upstream synthesis route of [ 387827-19-2 ]
  • Downstream synthetic route of [ 387827-19-2 ]

[ 387827-19-2 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 387827-18-1 ]
  • [ 387827-19-2 ]
YieldReaction ConditionsOperation in experiment
84% With hydrogen In ethanol at 20℃; for 48 h; A mixture of tert-butyl [4- (3-AMINOPHENYL)-3,] 6-dihydro- [1] [(2H)-PYRIDINECARBOXYLATE] (3.10 g, 11.3 mmol) and 10percent Pd/C (1.00 g) in ethanol (100 [ML)] was hydrogenated at room temperature using the balloon method for 2 days. The reaction mixture was filtered through Celite and washed with ethanol. The combined ethanol extracts were concentrated in vacuo and the residue was chromatographed on silica (dichloromethane: methanol: isopropylamine 95: 5: 1) to give the desired product (2.63 g, [84percent). 1H] NMR (400 MHz, [CDC13)] [8] 7.10 (t, 1H, J = 7.6 [HZ),] 6.62 (d, 1H, J [=] 8.4 Hz), 6.60-6. 59 (m, 2H), 4.27-4. 18 (m, 2H), 3.62-3. 58 (m, 2H), 2.80-2. 72 (m, 2H), 2.62-2. 59 (m, 1H), 1.89-1. 52 (m, 4H), 1.49 (s, 9H); ESMS m/e: [277.] 2 (M + H) [+.]
84% With hydrogen In ethanol at 20℃; for 48 h; A mixture of 3.10 g of tert-butyl 4-(3-aminophenyl)-1,2,3,6-tetrahydropyridine-1-carboxylate (11.3 mmol) and 1.0 g of 10percent Pd/C in 200 mL of ethanol was hydrogenated at room temperature using the balloon method for 2 days. The reaction mixture was filtered and washed with ethanol. The combined ethanol extracts were concentrated in vacuo and the residue was chromatographed on silica (dichloromethane:methanol 95:5 with 1percent isopropylamine added to protect the BOC group from hydrolysis) to give 2.63 g of the desired product (84percent). 1H NMR (400 MHz, CDCl3) δ 7.10 (t, 1H, J=7.60 Hz), 6.62 (d, 1H, J=8.4 Hz), 6.60-6.59 (m, 2H), 4.27-4.18 (m, 2H), 3.62-3.58 (m, 2H), 2.80-2.72 (m, 2H), 2.62-2.59 (m, 1H), 1.89-1.52 (m, 4H), 1.49 (s, 9H); ESMS m/e: 277.2 (M+H)+.
84% With hydrogen In ethanol at 20℃; for 48 h; A mixture of tert-butyl 4-(3-aminophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate (3.10 g, 11.3 mmol) and 10percent Pd/C (1.00 g) in ethanol (100 mL) was hydrogenated at room temperature using the balloon method for 2 days. The reaction mixture was filtered through Celite and washed with ethanol. The combined ethanol extracts were concentrated in vacuo and the residue was chromatographed on silica (dichloromethane:methanol:isopropylamine 95:5:1) to give the desired product (2.63 g, 84percent). 1H NMR (400 MHz, CDCl3) ? 7.10 (t, 1H, J=7.6 Hz), 6.62 (d, 1H, J=8.4 Hz), 6.60-6.59 (m, 2H), 4.27-4.18 (m, 2H), 3.62-3.58 (m, 2H), 2.80-2.72 (m, 2H), 2.62-2.59 (m, 1H), 1.89-1.52 (m, 4H), 1.49 (s, 9H); ESMS m/e: 277.2 (M+H)+.
84% With hydrogen In ethanol at 20℃; for 48 h; TERT-BUTYL 4-[3-(AMINO)PHENYL]-1-PIPERIDINECARBOXYLATE:
A mixture of tert-butyl 4-(3-aminophenyl)-3,6-dihydro-1(2H)-pyridinecarboxylate (3.10 g, 11.3 mmol) and 10percent Pd/C (1.00 g) in ethanol (100 mL) was hydrogenated at room temperature using the balloon method for 2 days.
The reaction mixture was filtered through Celite and washed with ethanol.
The combined ethanol extracts were concentrated in vacuo and the residue was chromatographed on silica (dichloromethane:
methanol:isopropylamine 95:5:1) to give the desired product (2.63 g, 84percent).
1H NMR (400 MHz, CDCl3) δ 7.10 (t, 1H, J=7.6 Hz), 6.62 (d, 1H, J=8.4 Hz), 6.60-6.59 (m, 2H), 4.27-4.18 (m, 2H), 3.62-3.58 (m, 2H), 2.80-2.72 (m, 2H), 2.62-2.59 (m, 1H), 1.89-1.52 (m, 4H), 1.49 (s, 9H); ESMS m/e: 277.2 (M+H)+.
63% With hydrogen In ethanol at 20℃; for 48 h; A mixture OF TERT-BUTYL 4- (3-AMINOPHENYL)-3, 6-DIHYDRO-1 (2H) -pyridinecarboxylate (3.30 g, 12.03 mmol) and 1.0 g of 10percent Pd/C in 200 mL ethanol was hydrogenated at rt for 2 days. The reaction mixture was filtered and washed with ethanol. The combined ethanol extracts were concentrated in vacuo to afford the desired product (2.1 g, 63percent). LC-MS M+H 276.7, RT 2. 0.5 1H NMR (DMSO): 6 6.9 (s, 1H), 6.4 (m, 3H), 4.9 (s, 2H), 4.0 (m, 2H), 2.7 (m, 2H), 1.7 (d, 2H), 1.4 (s, 9H).

Reference: [1] Patent: US2004/38855, 2004, A1,
[2] Patent: WO2004/5257, 2004, A1, . Location in patent: Page 54
[3] Patent: US6727264, 2004, B1, . Location in patent: Page column 56; 91
[4] Patent: US2005/154020, 2005, A1, . Location in patent: Page/Page column 8
[5] Patent: US2005/154022, 2005, A1, . Location in patent: Page/Page column 4; 9
[6] Patent: WO2004/58727, 2004, A1, . Location in patent: Page 52-53
  • 2
  • [ 138647-55-9 ]
  • [ 387827-19-2 ]
YieldReaction ConditionsOperation in experiment
86% With hydrogen In methanol at 35℃; for 3 h; Step 2; 4-(3-Amino-phenyl)-piperidine-1-carboxylic acid tert-butyl ester; A mixture of 4-(3-Nitro-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butylester (Example 12 Step 1, 950mg, 3.12mmol) and 10percentPd/C (catalytic amount) inmethanol (20ml) was stirred at 35°C for 3h under a hydrogen atmosphere. Thecatalyst was filtered off and the filtrate was concentrated in vacua to give a grey solid.Small amounts of diethyl ether (2x5ml) were added to the solid. After decantation andremoval of the solvent, the solid was dried in vacua to give title compound Example12 Step 2 as a white solid (800mg, 2.90mmol, 86percent).LCMS: Rt = 2.49min, m/z [M+23]+
Reference: [1] Patent: WO2006/10446, 2006, A2, . Location in patent: Page/Page column 37
[2] Patent: EP1371646, 2003, A1, . Location in patent: Page 37
[3] Patent: EP1342717, 2003, A1,
  • 3
  • [ 387827-18-1 ]
  • [ 75-31-0 ]
  • [ 387827-19-2 ]
Reference: [1] Patent: US2003/69261, 2003, A1,
[2] Patent: US2003/82623, 2003, A1,
  • 4
  • [ 1510865-58-3 ]
  • [ 387827-19-2 ]
YieldReaction ConditionsOperation in experiment
92% at 20 - 30℃; for 4 h; Weigh 4- (3-nitrophenyl) piperidine-1-carboxylate (4c)(2.4g, 7.8mmol), placed in100 ml round-bottom flask, the reaction flask was added 40mL methanol, are stirred hook. to the reaction flask was added palladium on carbon (0. 4g, 10percent w / w), stirred at room temperature for 4 hours. the methanol was removed under reduced pressure, column chromatography [(petroleum ether / ethyl acetate (v / ν) = 15: 1)] to give a white solid of 4- (3-aminophenyl) piperidine-1-carboxylate (intermediate 4) (2.0g, 92percent yield).
Reference: [1] Patent: CN105384695, 2016, A, . Location in patent: Paragraph 0204; 0214; 0215; 0216; 0217; 0218
  • 5
  • [ 591-19-5 ]
  • [ 375853-82-0 ]
  • [ 387827-19-2 ]
Reference: [1] Chemical Communications, 2017, vol. 54, # 1, p. 46 - 49
  • 6
  • [ 79099-07-3 ]
  • [ 387827-19-2 ]
Reference: [1] Patent: CN105384695, 2016, A,
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