1-Boc-4-[methoxy(methyl)carbamoyl]piperidine Chemical Properties

Melting point:

71.0 to 75.0 °C

Boiling point:

150°C/0.9mmHg(lit.)

Density 

1.106±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Dichloromethane, Ethyl Acetate, Methanol

form 

Oil

pka

-2.31±0.40(Predicted)

color 

Pale Yellow

InChI

InChI=1S/C13H24N2O4/c1-13(2,3)19-12(17)15-8-6-10(7-9-15)11(16)14(4)18-5/h10H,6-9H2,1-5H3

InChIKey

ITCQNWXLNZGEHP-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2933399990

1-Boc-4-[methoxy(methyl)carbamoyl]piperidine Usage And Synthesis

Chemical Properties

Pale Yellow Oil

Uses

An intermediate in the production of IKK inhibitors, ERK inhibitors, p38 MAP kinase inhibitors and serotonin receptor antagonists

Synthesis

The general procedure for the preparation of 1-Boc-4-[methoxy(methyl)carbamoyl]piperidine from 1-Boc-4-piperidinecarboxylic acid (2.34 g, 10.2 mmol) and dimethylhydroxylamine hydrochloride (1.5 g, 15 mmol) in DMF (50 mL) was as follows: to a stirred 1-Boc-4-piperidinecarboxylic acid and dimethylhydroxylamine hydrochloride at room temperature in a suspension in DMF was added triethylamine (2.8 mL, 20 mmol). After stirring for 10 min, HOBt (1.62 g, 12 mmol) and EDCI (2.3 g, 12 mmol) were added sequentially. The reaction mixture was stirred overnight and subsequently concentrated. The concentrated residue was dissolved in 1N HCl (100 mL) and extracted with EtOAc (3 × 100 mL). The organic phases were combined, washed sequentially with saturated NaHCO3 solution (50 mL), brine (50 mL), dried over MgSO4 and concentrated to give a colorless oily product (2.79 g, yield >100%). The product was characterized by 1H NMR (500 MHz, CDCl3) and MS (ESI+): 1H NMR δ 4.14 (m, 2H), 3.71 (s, 3H), 3.19 (s, 3H), 2.78 (m, 3H), 1.68 (m, 4H), 1.46 (s, 9H); MS (ESI+) m/z 217.72 (M+H+- Isobutene).

References

[1] Patent: US2004/14763, 2004, A1. Location in patent: Page 21
[2] Patent: WO2008/17461, 2008, A1. Location in patent: Page/Page column 61-62
[3] Patent: WO2008/108957, 2008, A2. Location in patent: Page/Page column 38
[4] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 4, p. 935 - 939
[5] Patent: WO2006/2434, 2006, A2. Location in patent: Page/Page column 39

1-Boc-4-[methoxy(methyl)carbamoyl]piperidine(139290-70-3)Related Product Information

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