1-(4-aminophenyl)piperidin-4-ol

1-(4-aminophenyl)piperidin-4-ol Property

Melting point:

158 °C

Boiling point:

404.2±40.0 °C(Predicted)

Density 

1.194±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

14.88±0.20(Predicted)

Appearance

Off-white to gray Solid

InChI

InChI=1S/C11H16N2O/c12-9-1-3-10(4-2-9)13-7-5-11(14)6-8-13/h1-4,11,14H,5-8,12H2

InChIKey

BJXPIIDUCADEKU-UHFFFAOYSA-N

SMILES

N1(C2=CC=C(N)C=C2)CCC(O)CC1

Safety

HazardClass 

IRRITANT

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P322Specific measures (see …on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

1-(4-aminophenyl)piperidin-4-ol Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 1-(4-aminophenyl)-4-hydroxypiperidine from 1-(4-nitrophenyl)piperidin-4-ol was as follows: 1-(4-nitrophenyl)piperidin-4-ol (1.50 g, 6.75 mmol) was dissolved in methanol (25 ml) and 10% palladium-carbon catalyst (150 mg) was added. The reaction system was replaced with hydrogen atmosphere and the reaction was stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was filtered through diatomaceous earth and the filter cake was washed with methanol. The filtrate and washings were combined and the solvent was removed by distillation under reduced pressure to afford the target product 1-(4-aminophenyl)-4-hydroxypiperidine (1.28 g, 99% yield). The structure of the product was confirmed by 1H-NMR (CDCl3/TMS) with the following chemical shifts δ ppm: 1.70-1.80 (m, 2H), 2.07 (br, 2H), 2.84 (br, 2H), 3.37 (br, 3H), 3.85 (br, 1H), 6.65 (d, J=8.4 Hz, 2H), 6.91 (br, 2H) .

References

[1] Patent: EP1988077, 2008, A1. Location in patent: Page/Page column 64-65
[2] Patent: WO2012/59932, 2012, A1. Location in patent: Page/Page column 112
[3] Patent: US2011/319413, 2011, A1. Location in patent: Page/Page column 11
[4] Patent: EP1775298, 2007, A1. Location in patent: Page/Page column 39
[5] Patent: US2007/32478, 2007, A1. Location in patent: Page/Page column 147