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ChemicalBook--->CAS DataBase List--->142643-29-6

142643-29-6

142643-29-6 Structure

142643-29-6 Structure
IdentificationMore
[Name]

3-N-Boc-Aminomethylpiperidine
[CAS]

142643-29-6
[Synonyms]

(3-AMINOMETHYL, N-BOC PROTECTED)PIPERIDINE
3-AMINOPIPERIDINE, 3-BOC PROTECTED
(+/-)-3-(BOC-AMINOMETHYL)PIPERIDINE
3-BOC-AMINOMETHYL PIPERIDINE
3-BOC-AMINOPIPERIDINE
3-N-BOC-AMINOMETHYL PIPERIDINE
(+/-)-3-N-BOC-AMINO-PIPERIDINE
3-N-BOC-AMINO PIPERIDINE
3-(TERT-BUTOXYCARBONYLAMINO)PIPERIDINE
CARBAMIC ACID, 3-PIPERIDINYL-, 1,1-DIMETHYLETHYL ESTER
PIPERIDIN-3-YL-CARBAMIC ACID TERT-BUTYL ESTER
PIPERIDIN-3-YLMETHYL-CARBAMIC ACID TERT-BUTYL ESTER
(R)-PIPERIDIN-3-YLMETHYL-CARBAMIC ACID TERT-BUTYL ESTER
(R,S)-(BOC-3-AMINOMETHYL)-PIPERIDINE
(S)-PIPERIDIN-3-YLMETHYL-CARBAMIC ACID TERT-BUTYL ESTER
TERT-BUTYL N-(3-PIPERIDYLMETHYL)CARBAMATE
TERT-BUTYL PIPERIDIN-3-YLCARBAMATE
TERT-BUTYL (PIPERIDIN-3-YLMETHYL) CARBAMATE
3-Aminopiperidine, 3-BOC protected 97%
3-BOC-3-AMINOPIPERIDINE
[Molecular Formula]

C11H22N2O2
[MDL Number]

MFCD03839941
[Molecular Weight]

214.3
[MOL File]

142643-29-6.mol
Chemical PropertiesBack Directory
[Melting point ]

60-70 °C(lit.)
[Boiling point ]

321.8±15.0 °C(Predicted)
[density ]

0.981
[storage temp. ]

2-8°C
[form ]

solid
[pka]

12.71±0.46(Predicted)
[color ]

White
[BRN ]

7023643
[CAS DataBase Reference]

142643-29-6(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

C,Xi
[Risk Statements ]

R34:Causes burns.
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
[RIDADR ]

UN 3259 8/PG 2
[WGK Germany ]

3
[Hazard Note ]

Irritant
[HazardClass ]

8
[HazardClass ]

IRRITANT
[HS Code ]

29333990
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethanol-->Ethyl acetate-->Dichloromethane-->Potassium carbonate-->Magnesium sulfate-->Triethylamine-->Ammonium hydroxide-->Sodium bicarbonate-->Hexane-->1,4-Dioxane-->Sodium borohydride-->Di-tert-butyl dicarbonate-->Calcium chloride-->Methanesulfonyl chloride-->Citric acid-->acetonitrile-->L-Glutamic acid dimethyl ester hydrochloride-->tert-butyl ((1-benzylpiperidin-3-yl)methyl)carbamate
Hazard InformationBack Directory
[Chemical Properties]

White powder
[Uses]

Reagent for:
Preparation of Tylophorine analogs
Enzymatic acylation
[Uses]

Reagent for:
  • Preparation of 9-substituted phenanthrene-based tylophorine analogs
  • Enzymatic acylation
[Synthesis]

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

220031-61-8

3-N-Boc-Aminomethylpiperidine

142643-29-6

To a solution of tert-butyl (1-benzylpiperidin-3-yl)methylcarbamate (2.05 g, 6.74 mmol, 1.0 equiv) in methanol (40 mL) was added 10% Pd(OH)2/C (0.21 g, 10 wt%). Cyclohexene (6.80 mL, 67.40 mmol, 10.0 eq.) was added to the reaction system under argon protection. The resulting suspension was refluxed under argon atmosphere for 20 hours. Upon completion of the reaction, it was filtered through a Celite pad (Celite 577 fine) and the filtrate was concentrated under reduced pressure to give the crude product. The crude product was purified by fast column chromatography with the eluent of dichloromethane/methanol/triethylamine (3:1:0.1, v/v/v) to afford 1.31 g of the target compound 3-Boc-aminomethylpiperidine as a colorless viscous oil. Yield: 91%; Thin Layer Chromatography Rf = 0.33 (dichloromethane/methanol/triethylamine = 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 x 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, CH2NHCOHBCH), 2.97-3.03 (m, 3H, CH2NHCOHBCH), 2.97-3.03 (m, 3H, CH2NHCO 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, 78.28, 155.86; ESI-HRMS m/z calculated C11H23N2O2 [M+H]+ 215.1760, measured 215.1763; IR (KBr) υ: 3385, 2978, 2934, 1685, 1528, 1458, 1367, 1272, 1254, 1174, 1009 cm-1 1174, 1009 cm-1.

[References]

[1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4442 - 4452
[2] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 2, p. 633 - 645
[3] Journal of Medicinal Chemistry, 2018, vol. 61, # 1, p. 119 - 139
Spectrum DetailBack Directory
[Spectrum Detail]

3-N-Boc-Aminomethylpiperidine(142643-29-6)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

142643-29-6(sigmaaldrich)
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