153473-24-6|tert-Butyl 4-(3-nitropyridin-2-yl)piperazine-1-carboxylate| Ambeed

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CAS No. :	153473-24-6
Formula :	C₁₄H₂₀N₄O₄
M.W :	308.33
SMILES Code :	O=C(N1CCN(C2=NC=CC=C2[N+]([O-])=O)CC1)OC(C)(C)C
MDL No. :	MFCD09028514
InChI Key :	FXKKCZGSSAXGMV-UHFFFAOYSA-N
Pubchem ID :	34180917

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Yield	Reaction Conditions	Operation in experiment
78%	With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; for 2h;	A mixture of tert-butyl 4-(3-nitropyridin-2-yl)piperazine-l -carboxylate 5 (350 mg, 1.14 mmol), Pd/C (60.4 mg, 10%, 0.0568 mmol) and MeOH (6 ml) was subjected to the hydrogenation condition with hydrogen balloon at room temperature. After stirring for 2 h, the resulting solution was filtered through celite. The resulting organic solution was concentrated under reduced pressure and purified by silica gel column chromatography (Hexane/EtOAc/CH2Cl2 = 1 : 1 : 1) to give tert-butyl 4-(3-aminopyridin-2-yl)piperazine-l -carboxylate (246 mg, 78%) as a white powder. MS (EI) for Ci4H22 402: 279.2 (MH+).
69%	With hydrogen;palladium on activated charcoal; In ethanol; under 1034.32 Torr; for 2h;	Example 18.1: 4-(3-Ammo-pyridin-2-yl)-piperazine-l-carboxylic acid tert-butyl ester. A mixture of 4-(3-nitro-pyridin-2-yl)-piperazine-l-carboxylic acid tert-tmtyl ester (4.0 g, 12,97 mmol), palladium (on activated carbon, 500 mg) and ethanol (150 mL) was shaken under 20 psi of hydrogen for 2 hours. The reaction mixture was filtered through Diatomaceous earth and concentrated to give 4-(3-amino-pyridin-2-yl)-piperazine-l- carboxylic acid tert-butyl ester (2.5 g, 69 %). GC/MS m/z 278, 205, 134, 148, 109, 93, 57.
	With palladium(II) hydroxide; In methanol; cyclohexene; at 70℃; for 2h;	Synthesis of 3-Amino-2-(Boc-piperazinyl)pyridine 7: 3-Nitro-2-(Boc-piperazine)pyridine 6 (1.765 g, 5.72 mmol) was dissolved in methanol (15 mL) at room temperature. Then Pd(OH)2 (1.234 g) and cyclohexene (2.0 mL, 19.52 mmol) were added. The resulting mixture was heated at 70 C. for 2 h. The mixture was concentrated to remove the solvent. DCM was added and then it was filtered through a pad of silica gel, washed with DCM and 10% MeOH/DCM. The collected solution was concentrated and dried under high vacuum to afford a slight pink solid as the product (1.384 g, 87% yield). 1H-NMR (CDCl3): 7.794 (dd, J=5.0 Hz and 1.5 Hz, 1 H, Ar-H), 6.956 (dd, J=7.5 Hz and 1.5 Hz, 1 H, Ar-H), 6.854 (dd, J=7.5 Hz and 5.0 Hz, 1 H, Ar-H), 3.783 (br, 2 H, NH2), 3.571 (t, J=4.5-5.0 Hz, 4 H, 2 CH2), 3.059 (t, J=4.5-5.0 Hz, 4 H, 2 CH2), 1.482 (s, 9 H, 3 CH3). LC-MS: 279.2 (MH+). (ref. Romero D. L. et al. J. Med. Chem. 37, 999-1014, 1994.) Synthesis of 2-(Boc-piperazinyl)-3-(isopropylamino)pyridine 4:

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CAS No.: 153473-24-6

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CAS No.: 153473-24-6

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H204	Fire or projection hazard
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H220	Extremely flammable gas
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H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
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H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed