ChemicalBook CAS DataBase List 3-N-Boc-Aminomethylpiperidine

3-N-Boc-Aminomethylpiperidine synthesis

7synthesis methods

Product Name:3-N-Boc-Aminomethylpiperidine
CAS Number:142643-29-6
Molecular formula:C11H22N2O2
Molecular Weight:214.3

tert-butyl ((1-benzylpiperidin-3-yl)methyl)carbamate

220031-61-8
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142643-29-6
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Yield:142643-29-6 91%

Reaction Conditions:

with 10% palladium hydroxide on charcoal;cyclohexene in methanol for 20 h;Inert atmosphere;Reflux;

Steps:

Tert-butyl piperidin-3-ylmethylcarbamate (4a)
To a solution of tert-butyl (1-benzylpiperidin-3-yl)methylcarbamate (2.05 g, 6.74 mmol, 1.0equiv.) in MeOH (40 mL), 10% Pd(OH)2 on carbon (0.21 g, 10% mass of tert-butyl (1-benzylpiperidin-3-yl)methylcarbamate) and cyclohexene (6.80 mL, 67.40 mmol, 10.0 equiv.) were added under an argon atmosphere. The resulting suspension was refluxed under an argon atmosphere for 20 h, filtered through a pad of Celite (Celite, 577 fine), and evaporated to obtain a crude product, which was purified by flash column chromatography using DCM/MeOH/Et3N = 3/1/0.1 as eluent, to obtain 1.31 g of the compound as a viscous oil. Yield: 91%; colorless oil; Rf = 0.33 (DCM/MeOH/Et3N = 3/1/0.1); 1H NMR (400 MHz,CDCl3): δ 1.08 (qd, J = 11.2, 4.0 Hz, 1H, CH2CHAHBCH), 1.42 (s, 9H, 3 × CH3), 1.45-1.52(m, 1H, CHAHBCH2CH), 1.58-1.70 (m, 2H, CHAHBCHAHBCH), 1.76-1.82 (m, 1H, CH), 2.32(t, J = 11.2 Hz, 1H, NHCHAHBCH), 2.52-2.60 (m, 2H, CH2CHAHBNH), 2.97-3.03 (m, 3H,CH2NHCO + CH2CHAHBNH), 3.06 (dd, J = 11.6, 3.2 Hz, 1H, NHCHAHBCH), 4.63 (br s, 1H,NHCO); 13C NMR (100 MHz, CDCl3): δ 24.99, 27.97, 28.27, 36.86, 43.74, 45.90, 49.54,S478.28, 155.86; ESI-HRMS m/z calcd. for C11H23N2O2 [M+(H)]+ 215.1760, found 215.1763;IR (KBr) υ = 3385, 2978, 2934, 1685, 1528, 1458, 1367, 1272, 1254, 1174, 1009 cm-1.

References:

Knez, Damijan;Brus, Boris;Coquelle, Nicolas;Sosič, Izidor;Šink, Roman;Brazzolotto, Xavier;Mravljak, Janez;Colletier, Jacques-Philippe;Gobec, Stanislav [Bioorganic and Medicinal Chemistry,2015,vol. 23,# 15,p. 4442 - 4452] Location in patent:supporting information

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