3-N-Boc-Aminomethylpiperidine
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3-N-Boc-Aminomethylpiperidine
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CAS No:
142643-29-6
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Formula:
C11H22N2O2
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Chemical Name:
3-N-Boc-Aminomethylpiperidine
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Synonyms:
3-N-BOC-AMINOMETHYL PIPERIDINE;3-AMINOPIPERIDINE, 3-BOC PROTECTED;(3-AMINOMETHYL, N-BOC PROTECTED)PIPERIDINE;(+/-)-3-(BOC-AMINOMETHYL)PIPERIDINE;3-BOC-AMINOMETHYL PIPERIDINE;3-BOC-AMINOPIPERIDINE;CARBAMIC ACID, 3-PIPERIDINYL-, 1,1-DIMETHYLETHYL ESTER;TERT-BUTYL (PIPERIDIN-3-YLMETHYL) CARBAMATE
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CAS No:
Characteristics
50.4
1.2
Off-white solid
0.981
60-70 °C(lit.)
321.8±15.0 °C(Predicted)
148.4±20.4 °C
1.458
2-8°C
0.00029mmHg at 25°C
Safety Information
8
UN 3259 8/PG 2
3
34
26-36/37/39-45
C,Xi
Irritant
P280-P305 + P351 + P338-P310
H314
|Danger|H314 (97.56%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, and P501|Aggregated GHS information provided by 41 companies from 2 notifications to the ECHA C&L Inventory.
3-N-Boc-Aminomethylpiperidine Use and Manufacturing
To a solution of tert-butyl (1-benzylpiperidin-3-yl)methylcarbamate (2.05 g, 6.74 mmol, 1.0equiv.) in MeOH (40 mL), 10percent Pd(OH)2 on carbon (0.21 g, 10percent 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: 91percent; 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.
Computed Properties
Molecular Weight:214.30
XLogP3:1.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:214.168127949
Monoisotopic Mass:214.168127949
Topological Polar Surface Area:50.4
Heavy Atom Count:15
Complexity:211
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
