4-N-BOC-Aminopiperidine Chemical Properties

Melting point:

162-166 °C(lit.)

Boiling point:

80°C/0.05mm

Density 

1.02±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

12.39±0.20(Predicted)

form 

Crystalline Powder

color 

Off-white

Sensitive 

Air Sensitive

InChI

InChI=1S/C10H20N2O2/c1-10(2,3)14-9(13)12-8-4-6-11-7-5-8/h8,11H,4-7H2,1-3H3,(H,12,13)

InChIKey

CKXZPVPIDOJLLM-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NC1CCNCC1

CAS DataBase Reference

73874-95-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

4-N-BOC-Aminopiperidine Usage And Synthesis

Description

4-(N-Boc-amino)piperidone may be used as a functionalization reagent for introduction of a primary and a tertiary amino group to poly(2-isopropyl-2-oxazoline. It can also be used as pharma building block. It is used in the synthesis of a piperidine-4-carboxamide CCR5 antagonist with potent anti-HIV 1-activity. It is an intermediate for the synthesis of various pharmaceutical and biologically active compounds, including inhibitors and therapeutic agents. It is used for the synthesis of diphenyl purine derivatives as peripherally selective cannabinoid receptor 1 Antagonists.

Chemical Properties

off-white crystalline powder

Uses

Pharma building block.

General Description

4-(N-Boc-amino)piperidone is a piperidone derivative.

Synthesis

General procedure for the synthesis of 4-tert-butoxycarbonylaminopiperidine from tert-butyl (1-benzylpiperidin-4-yl)carbamate: N-butyl-1-benzylpiperidin-4-ylcarbamate (3.80 g, 13.1 mmol) was dissolved in 26 mL of methanol in a 100 mL reaction vessel. A catalytic amount of 10% palladium/carbon (Pd/C) was added. The reaction was stirred under hydrogen atmosphere for 12 hours. Upon completion of the reaction, the palladium/carbon catalyst was removed by filtration through a diatomaceous earth pad and the filtrate was concentrated under reduced pressure to remove the solvent. The resulting residue was purified by silica gel column chromatography to afford 4-tert-butoxycarbonylaminopiperidine (2.64 g, 99% yield). The product was confirmed by 1H-NMR (200 MHz, CD3OD): δ 1.36 (s, 9H), 1.84-2.36 (m, 4H), 2.74 (m, 2H), 3.42 (m, 2H), 3.60 (br, 1H).LC/MS analysis showed the [M+H]+ peak as 201.

References

[1] Patent: WO2008/54154, 2008, A1. Location in patent: Page/Page column 33; 34; 76; 77; 162-164
[2] Patent: WO2007/52938, 2007, A1. Location in patent: Page/Page column 18
[3] Journal of Medicinal Chemistry, 1999, vol. 42, # 14, p. 2706 - 2715
[4] Patent: WO2007/46550, 2007, A1. Location in patent: Page/Page column 117
[5] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 24, p. 5345 - 5352

4-N-BOC-Aminopiperidine(73874-95-0)Related Product Information

• 1-Aminopiperidine
• DROPERIDOL
• Haloperidol
• 3-N-Boc-aminopiperidine
• tert-butyl thiazol-4-ylcarbamate
• (1R,4R)-(4-MethylaMino-cyclohexyl)-carbaMic acid tert-butyl ester
• 1-Oxa-6-azaspiro[3.3]heptane-6-carboxylic acid, 3,3-diMethyl-, 1,1-diMethylethyl ester
• tert-butyl((5-carbamoyl-1-methyl-1H-pyrazol-3-yl)methyl)(methyl)carbamate
• DI-TERT-BUTYL ETHER
• Carbamic acid, N-methyl-N-[(3-nitrophenyl)methyl]-, 1,1-dimethylethyl ester
• 4-AMINO-1-BOC-PIPERIDINE-4-CARBOXYLIC ACID
• 4-TERT-BUTOXYCARBONYLAMINO-PIPERIDINE-1,4-DICARBOXYLIC ACID MONOBENZYL ESTER
• 4-N-Boc-4-N-Methyl-aminopiperidine
• 1-BENZYL-4-(N-BOC-AMINO) PIPERIDINE 98
• 4-TERT-BUTOXYCARBONYLAMINO-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER
• Diphenoxylate
• (R)-3-(Boc-Amino)piperidine
• (R)-1-Benzyl-3-N-Boc-aminopiperidine