4-(2-Aminoethyl)-1-Boc-piperidine Chemical Properties

Boiling point:

316.0±15.0 °C(Predicted)

Density 

1.010±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

semisolid

pka

10.43±0.10(Predicted)

color 

off-white to light yellow

InChI

InChI=1S/C12H24N2O2/c1-12(2,3)16-11(15)14-8-5-10(4-7-13)6-9-14/h10H,4-9,13H2,1-3H3

InChIKey

LBQDLHPFISVBRU-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC(CCN)CC1

CAS DataBase Reference

146093-46-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39

RIDADR 

UN2811

WGK Germany 

WGK 3

HazardClass 

IRRITANT

HS Code 

2933399990

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral

4-(2-Aminoethyl)-1-Boc-piperidine Usage And Synthesis

Uses

A semi-flexible linker useful for PROTAC development for targeted protein degradation. Incorporation of rigidity into the linker region of PROTACs may impact degradation kinetics as well as drug design (absorption; distribution; metabolism; excretion; and toxicity; ADMET) properties of PROTACs.
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Synthesis

General procedure for the synthesis of 2-(N-Boc-4-piperidinyl)ethylamine from 1-Boc-4-(cyanomethyl)piperidine: tert-butyl 4-(cyanomethyl)piperidine-1-carboxylate (20 g, 89.29 mmol) and NH4OH (9 mL) were dissolved in methanol (200 mL) and Raney Ni (6 g, 101.69 mmol) was added. The reaction was carried out at 50°C for 5 h under H2 pressure of 50 psi. Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad and the filtrate was concentrated to afford the target product 2-(N-Boc-4-piperidinyl)ethylamine (20.5 g, 100%) as a colorless oil.1H NMR (400 MHz, CDCl3) δ 1.06-1.19 (m, 2H), 1.44 (d, J = 7.41 Hz, 2H), 1.47 (s 9H), 1.50-1.58 (m, 1H), 1.66 (d, J = 12.49 Hz, 2H), 2.09 (br.s., 2H), 2.70 (t, J = 12.29 Hz, 2H), 2.75-2.83 (m, 2H), 4.08 (br.s., 2H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4805 - 4811

4-(2-Aminoethyl)-1-Boc-piperidine(146093-46-1)Related Product Information

• CARBONYL SULFIDE
• Benzyltriethylammonium chloride
• DROPERIDOL
• 2-(2-Aminoethylamino)ethanol
• Haloperidol
• 2,2,6,6-Tetramethyl-4-piperidinol
• Carbonyl iron powder
• Piperidine
• Diphenoxylate
• 3-(2-AMINOETHYL)-1-BOC-PIPERIDINE
• 4-aminoethyl-n-boc-piperidine,2-(2-AMINOETHYL)-1-BOC-PIPERIDINE,2-(AMINOETHYL)-1-BOC-PIPERIDINE
• N-ALPHA-FMOC-BETA-(1-BOC-PIPERIDIN-4-YL)-D,L-ALANINE
• (4-[[(3,4-DICHLOROPHENYL)SULFONYL]AMINO]PHENYL)ACETIC ACID
• tert-Butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate
• 4-(2-Aminoethyl)-1-Boc-piperidine
• N-[3-METHYL-4-(2-OXO-2H-CHROMEN-3-YL)PHENYL]BENZENESULFONAMIDE
• (S)-N-TFA-N'-BOC-4-PIPERIDYLALANINE
• (4-[[(2-NITROPHENYL)SULFONYL]AMINO]PHENYL)ACETIC ACID