1086063-19-5|1'-Benzylspiro[indoline-3,4'-piperidin]-2-one| Ambeed

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CAS No. :	1086063-19-5
Formula :	C₁₉H₂₀N₂O
M.W :	292.37
SMILES Code :	O=C1NC2=C(C=CC=C2)C13CCN(CC4=CC=CC=C4)CC3
MDL No. :	MFCD11935879

Yield	Reaction Conditions	Operation in experiment
90.2%	With hydrogen In methanol at 20℃; for 15 h;	Process 1Production of spiro(indole-3,4'-piperidine)-2(1H)-oneSpiro(indole-3,4'-piperidine)-2(1H)-one was produced by the method described below.Under an argon atmosphere, a tetrahydrofuran solution (20 mL) of oxindole (3.00 g, 22.5 mmol) and a tetrahydrofuran solution (20 mL) of benzylbis(2-chloroethyl)amine (5.20 g, 22.5 mmol) were added sequentially to a tetrahydrofuran solution (100 mL) of sodium hydride (1.60 g, 67.6 mmol) at room temperature. The mixture was stirred at the same temperature for 1 hour and further stirred at 90° C. for 3 hours. The reaction solution was cooled to room temperature, and then added with a tetrahydrofuran solution (10 mL) of sodium hydride (0.540 g, 22.5 mmol) and stirred further at 90° C. for 12 hours. The reaction solution was added with saturated ammonium-chloride aqueous solution and stirred at room temperature for 10 minutes. The mixed solution was poured into the mixed solution of a saturated aqueous solution of sodium hydrogen carbonate and brine, then extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, followed by a vacuum concentration. The resultant residue was purified by silica-gel chromatography (chloroform:methanol=20:1) and 1'-benzylspiro(indole-3,4'-piperidine)-2(1H)-one (2.94 g, 44.6percent) was obtained as a yellow amorphous solid.¹H-NMR (400 MHz, CDCl₃) δ; 1.78-1.93 (m, 2H), 1.95-2.06 (m, 2H), 2.65-2.77 (m, 2H), 2.87-3.00 (m, 2H), 3.69 (s, 2H), 6.90 (d, J=7.6 Hz, 1H), 7.02(t, J=7.6 Hz, 1H), 7.20 (t, J=7.6 Hz, 1H), 7.26 (t, J=6.2 Hz, 1H), 7.34 (t, J=7.6 Hz, 2H), 7.40-7.41(m, 3H), 8.72 (s, 1H).To a methanol solution (5 mL) of 1'-benzylspiro(indole-3,4'-piperidine)-2(1H)-one (300 mg, 1.03 mmol), 10percent palladium carbon (30.0 mg) was added. The mixture was stirred under a hydrogen atmosphere at room temperature for 15 hours. The reaction solution was filtered using celite followed by a vacuum concentration, and spiro(indole-3,4'-piperidine)-2(1H)-one (187 mg, 90.2percent) was obtained as a colorless amorphous solid.¹H-NMR (400 MHz, CDCl₃) δ; 1.73-1.78 (m, 2H), 1.88-1.94 (m, 2H), 3.06-3.12 (m, 2H), 3.35-3.41 (m, 2H), 6.92 (d, J=7.7 Hz, 1H), 7.04 (t, J=7.7 Hz, 1H), 7.22 (t, J=7.7 Hz, 1H), 7.42 (d, J=7.7 Hz, 1H), 8.70 (br, 1H).
78%	With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 15 h;	Step 2A solution of 1’-benzylspiro[indoline-3,4’-piperidin]-2-one 2a (5 g, 17.10 mmol, 1 eq.)in methanol (100 ml) was hydrogenated at RT with 10percent Pd/C (0.18 g) as a catalyst for15h. The catalyst was filtered off and the solvent was evaporated under vacuum. Theresidue was then recrystallized from DIPE/acetonitrile to give 2.7 g (78percent yield) of spiro [indoline-3 ,4’-piperidin] -2-one 2b.

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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 1086063-19-5

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CAS No.: 1086063-19-5

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