N-Boc-4-iodopiperidine

N-Boc-4-iodopiperidine Property

Melting point:

35-38°

Boiling point:

318.8±35.0 °C(Predicted)

Density 

1.50±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

pka

-2.54±0.40(Predicted)

form 

Crystalline Powder or Low Melting Solid

color 

White to pale brown

Water Solubility 

Slightly soluble in water. Soluble in methanol.

Sensitive 

Light Sensitive

InChI

InChI=1S/C10H18INO2/c1-10(2,3)14-9(13)12-6-4-8(11)5-7-12/h8H,4-7H2,1-3H3

InChIKey

YFWQFKUQVJNPKP-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

301673-14-3

Safety

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

22-26-36/37/39

HazardClass 

IRRITANT

HS Code 

29389090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

N-Boc-4-iodopiperidine Chemical Properties,Usage,Production

Chemical Properties

White powder

Uses

Used in the coupling reaction in Iron-and Cobalt-Catalyzed Arylation of Azetidines, Pyrrolidines, and Piperidines with Grignard Reagents.

Synthesis

The general procedure for the synthesis of N-Boc-4-iodopiperidine from N-Boc-4-hydroxypiperidine was as follows: to a solution of N-Boc-4-hydroxypiperidine (10.0 g, 49.7 mmol) in dichloromethane (200 mL) was added triphenylphosphine (16.9 g, 64.6 mmol) and imidazole (5.07 g, 74.5 mmol) sequentially. After the reaction mixture was cooled to 0°C in an ice bath, iodine (15.1 g, 59.6 mmol) was added slowly in portions. After addition, the reaction mixture was stirred at room temperature for 18 hours. After completion of the reaction, the reaction solution was diluted with water and extracted with ether. The organic layers were combined, washed sequentially with water and saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure and the residue was ground with hexane to remove excess triphenylphosphine and triphenylphosphine oxide. After filtration, the filtrate was concentrated under reduced pressure to afford the target product N-Boc-4-iodopiperidine as a colorless oil (14.4 g, 93% yield).

References

[1] Patent: US2005/9838, 2005, A1. Location in patent: Page 143
[2] Patent: WO2018/106636, 2018, A1. Location in patent: Paragraph 00283
[3] Patent: WO2011/143366, 2011, A1. Location in patent: Page/Page column 45
[4] Journal of Organic Chemistry, 2004, vol. 69, # 15, p. 5120 - 5123
[5] Synlett, 1998, # 4, p. 379 - 380