4-(Boc-Aminomethyl)piperidine Chemical Properties

Melting point:

106 °C

Boiling point:

321.8±15.0 °C(Predicted)

Density 

0.981±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in DMSO.

pka

12.72±0.46(Predicted)

form 

powder to crystal

color 

White to Almost white

CAS DataBase Reference

135632-53-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,Xi

Risk Statements 

34-36/38

Safety Statements 

26-36/37/39-45

RIDADR 

3259

Hazard Note 

Corrosive

HazardClass 

IRRITANT

HazardClass 

8

PackingGroup 

Ⅲ

HS Code 

29333990

4-(Boc-Aminomethyl)piperidine Usage And Synthesis

Chemical Properties

4-Boc-aminomethylpiperidine contains a piperidine ring and an aminomethyl group, and the aminomethyl group is protected by a tert-butoxycarbonyl (Boc) group. This compound is commonly used as an intermediate in organic synthesis. The Boc protecting group is a common protecting group that protects the amine group in organic synthesis reactions. By adding the Boc protecting group, the amine group can be prevented from unwanted reactions while allowing other chemical reactions to take place. The tert-butoxycarbonyl protecting group can be removed under appropriate conditions before the amine group needs to be reduced.

Uses

4-(Boc-aminomethyl)piperidine is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff.

Synthesis

General procedure: 4-aminomethylpiperidine (3.6 g) and 1-BOC-imidazole (5.3 g) were dissolved in toluene (80 mL), and the reaction was stirred at 25°C overnight. After completion of the reaction, the solution was concentrated and the residue was purified by silica gel column chromatography (eluent: EtOAc/hexane=1/2) to afford Intermediate 227-I (4.7 g) in 70% yield. Intermediate 227-I (4.7 g) and triethylamine (2.7 mL) were dissolved in 1-pentanol (20 mL), 2,4-dichloro-6-aminopyrimidine (5.4 g) was added, and the reaction was carried out at 120 °C for 12 hours. After completion of the reaction, the solvent was removed and the residue was purified by silica gel column chromatography (eluent: EtOAc/hexane=1/9) to afford Intermediate 227-II (5.2 g) in 70% yield. Intermediate 227-II (1.0 g) was treated with 1 M HCl (20 mL) in CH2Cl2 (10 mL) and stirred at room temperature for 8 hours. After completion of the reaction, the solution was concentrated, the residue neutralized with NH4OH and extracted with CH2Cl2. The organic layer was separated and concentrated, and the residue was purified by silica gel column chromatography (eluent: MeOH) to afford Intermediate 227-III (636 mg) in 90% yield. Intermediate 222-III (790 mg) was added to a solution of intermediate 227-III (450 mg) in MeOH (20 mL) and stirred at 25 °C for 2 hours. Then NaBH(OAc)3 (2.0 g) was added and the reaction was continued at 25 °C for 12 hours. After completion of the reaction, the solution was concentrated, saturated NaHCO3 solution was added and extracted with CH2Cl2. The organic layer was separated and concentrated, and the residue was purified by silica gel column chromatography (eluent: MeOH) to afford intermediate 227-IV (539 mg) in 60% yield. N1-morpholino-N1-piperazine ethane (240 mg) was added to a 1-pentanol (1 mL) solution of Intermediate 227-IV (160 mg) and stirred at 120 °C for 8 hours. After completion of the reaction, the solution was concentrated and the residue was purified by silica gel column chromatography (eluent: EtOAc/MeOH=5/1) to afford Intermediate 227-V (85 mg) in 40% yield. 20% TFA/CH2Cl2 (1 mL) was added to a solution of CH2Cl2 (1 mL) of intermediate 227-V (85 mg) and stirred at room temperature for 8 hours. After completion of the reaction, the solvent was removed and the residue was purified by silica gel column chromatography (eluent: 21% NH3(aq)/MeOH=1/19) to afford compound 227 (65 mg) in 90% yield. Finally, compound 227 was treated with a solution of CH2Cl2 (1 mL) in 1M HCl (1 mL) for 0.5 hours. After removal of the solvent, the residue was treated with ether and filtered to give the hydrochloride salt of compound 227.CI-MS (M++1): 544.4.

References

[1] Patent: US2006/281712, 2006, A1. Location in patent: Page/Page column 108-109

4-(Boc-Aminomethyl)piperidine(135632-53-0)Related Product Information

• 2,2,6,6-Tetramethyl-4-piperidinol
• 2,2,6,6-Tetramethylpiperidinooxy
• 4-Aminobenzoic acid
• tert-Butanol
• 2-Butoxyethanol
• tert-Butyl carbamate
• Diethylene glycol monobutyl ether
• Urethane
• Buprofezin
• Hexamethyldisilazane
• tert-Butyl acetate
• tert-Butyl peroxybenzoate
• tert-Butyl peroxyacetate
• Methyl anthranilate
• 2-Amino-2-methyl-1-propanol
• Haloperidol
• 4-(Aminomethyl)piperidine
• tert-Butyl 4-aminobenzoate