308386-35-8|tert-Butyl 4-(pyridin-4-yloxy)-piperidine-1-carboxylate| Ambeed

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CAS No. :	308386-35-8
Formula :	C₁₅H₂₂N₂O₃
M.W :	278.35
SMILES Code :	O=C(N1CCC(OC2=CC=NC=C2)CC1)OC(C)(C)C
MDL No. :	MFCD09261175

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Yield	Reaction Conditions	Operation in experiment
98%	With platinum(IV) oxide; palladium on activated carbon; hydrogen; acetic acid; at 55℃; for 16h;	To a stirred solution of tert-butyl 4-(pyridin-4-yloxy)piperidine-1-carboxylate (6.00 g, 21.6 mmol,) in AcOH (150.00 mL) were added anhydrous PtO2(900.00 mg, 3.963 mmol) and Pd/C (600.00 mg, 0.564 mmol, 10 wt%) at room temperature under nitrogen atmosphere. The mixture was hydrogenated at 55 C for 16 h under hydrogen atmosphere using a hydrogen balloon at room temperature. The mixture was then filtered through a Celite pad and the filter cake was washed with CH2Cl2 (3 × 50 mL). The filtrates were evaporated under reduced pressure, and H2O was added to the residue. Then, NH3H2O (20 wt%) was added dropwise to adjust the pH to 10, and the mixture was extracted CH2Cl2(3 × 100 mL).The collected organic layers were dried, filtered, and concentrated to afford tert-butyl 4-(piperidin-4-yloxy)piperidine-1-carboxylate (6 g, 98%) as a colorless oil;1H NMR (400 MHz, Chloroform-d) d 3.96-3.67 (m, 3H), 3.62-3.56 (m, 1H), 3.51-3.45 (m, 1H), 3.15-2.97 (m, 4H), 2.65-2.58 (m, 2H), 1.95-1.70 (m, 6H), 1.54-1.38 (m, 11H); LC/MS (ESI, m/z): [(M + 1)]+ = 285.2.
60%		Pyridyl ether IA (1 g, 3.6 mmol) was dissolved in 20 mL of absolute ethanol. The solution was degassed under vacuum, and placed under nitrogen atmosphere. Platinum oxide (0.25 g, 0.25 weight equiv.) was added and the resulting mixture was degassed again, then <n="45"/>placed under nitrogen atmosphere. Concentrated sulfuric acid (0.19 mL, 3.6 mmol) was added, the reaction was degassed a third time, and then put under H2 atmosphere using a gas-filled balloon. The reaction was allowed to stir at room temperature for about 14 hours and was then poured into 50 mL of an ice cold 1.0 M NaOH aqueous solution. The resulting solution was rinsed with a small volume OfCH2Cl2, and filtered through a Celite pad. The organic solvent was removed in vacuo and the remaining aqueous solution was extracted with CH2Cl2 (50 mL x 3). The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated in vacuo to provide an oily residue, which was purified using flash column chromatography, eluting with CH2Cl2-MeOH (10:1, 5:1, and 1 :1, v/v) to provide 0.61g of bis- N-heterocylic alkyl ether IB (60%, MH+ = 285.21 ).
	With hydrogen; acetic acid;5% rhodium on alumina; under 2585.81 Torr;	EXAMPLE 11 Preparation of 4-(Piperidin-4-yloxy)piperidine-1-carboxylic acid tert-butyl ester (41). To 1.0 g (3.6 mmol) of 4-(pyridin-4-yloxy)piperidine-1-carboxylic acid tert-butyl ester (40) dissolved in 4.0 mL of HOAc was added 0.2 g of 5% Rh/Al2O3. The reaction mixture was put under 50 psi of H2 gas overnight, filtered through Celite and the solvent was removed by rotary evaporation to yield 41 as a colorless oil.

0.5 g	With palladium 10% on activated carbon; hydrogen; acetic acid; In ethanol; at 80℃; under 30003.0 Torr; for 16h;	To a 500 ml round bottom flask, purged and maintained under inert atmosphere, were added tert- butyl 4-(pyridin-4-yloxy)piperidine-1 -carboxylate (2 g, 7.2 mmol), EtOH (100 ml), AcOH (5 ml) and Pd/C (10%) (0.4 g). The RM was stirred at 80C for 16 h under an atmosphere of hydrogen (4 MPa). The mixture was filtered through Celite, the filtrate was concentrated and purified by chromatography on silica gel eluting with MeOH in DCM (1 :10) yielding the title compound as an oil (0.5 g).Method D: Rt = 1 .32 min; MS m/z [M+H]+285.3.
0.5 g	With palladium on activated charcoal; hydrogen; acetic acid; In ethanol; at 80℃; under 30003.0 Torr; for 16h;	In a 500 ml round bottom flask, purged and maintained under inert atmosphere were mixed tert- butyl 4-(pyridin-4-yloxy)piperidine-1 -carboxylate (2 g, 7.2 mmol), EtOH (100 ml), AcOH (5 ml) and palladium on carbon (0.4 g). The RM was stirred at 80C for 16 h under under H2 atmosphere (4 MPa). The mixture was filtered through Hyflo, and the filtrate was concentrated under reduced pressure. Purification of the crude mixture by chromatography on silica gel eluting with 10% MeOH in DCM afforded 0.5 g of the title compound as a colorless oil.LC-MS (method H): Rt = 1 .32 min, [M+H]+ = 285.3.
31 g	With palladium 10% on activated carbon; hydrogen; acetic acid; In ethanol; at 80℃; under 45004.5 Torr; for 24h;	To a 500 ml high pressure reactor were added tert-butyl 4-(pyridin-4- yloxy)piperidine-1-carboxylate (32 g, 115 mmol), Pd/C (10 %, 9.6 g), EtOH (300 ml) and HOAc (30 ml). The mixture was stirred under H2 atmosphere (60 bar) at 80 C for 24 h. The mixture was cooled to RT and filtered. The filtrate was diluted with DCM (1 L) and the organic phase was washed with an aq. solution of NaOH (2 M, 2 x 200 mL), water (200 mL), brine (2 x 100 ml) and dried over Na2SO4, yielding the title compound as a solid (31 g). Method B: Rt = 1.96 min; [M+H]+= 285.

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CAS No.: 308386-35-8

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CAS No.: 308386-35-8

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Precautionary Statements-General
Code	Phrase
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Prevention
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Health hazards
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