3-N-Boc-Aminomethylpiperidine Chemical Properties

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 Information

Hazard Codes 

C,Xi

Risk Statements 

34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3259 8/PG 2

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

8

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

3-N-Boc-Aminomethylpiperidine Usage And Synthesis

Chemical Properties

White powder

Uses

Reagent for:

• Preparation of 9-substituted phenanthrene-based tylophorine analogs
• Enzymatic acylation

Uses

Reagent for:
Preparation of Tylophorine analogs
Enzymatic acylation

Synthesis

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

3-N-Boc-Aminomethylpiperidine(142643-29-6)Related Product Information

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