spiro[isochroman-1,4'-piperidine]

spiro[isochroman-1,4'-piperidine] Property

Boiling point:

341.3±42.0 °C(Predicted)

Density 

1.12

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

10.21±0.20(Predicted)

Appearance

White to off-white Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

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

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

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

spiro[isochroman-1,4'-piperidine] Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of spiro[isobenzodihydropyran-1,4'-piperidine]-1'-carboxylic acid tert-butyl ester from spiro[isobenzodihydropyran-1,4'-piperidine] is as follows: Step 1: Deprotection reaction Trifluoroacetic acid (15 mL) was added to a solution of tert-butyl spiro[isobenzodihydropyran-1,4'-piperidine]-1'-carboxylate (3.3 g, 10.87 mmol) in dichloromethane (15 mL), and the reaction was stirred for 2 h at room temperature. Step 2: Post-treatment The reaction mixture was concentrated under reduced pressure and the residue was redissolved in dichloromethane (15 mL). Alkalization was carried out by adjusting the pH to 8 with aqueous sodium carbonate. The organic and aqueous phases were separated and the organic phase was washed sequentially with water, sodium bicarbonate solution and saturated saline. The organic phase was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. Step 3: Purification The obtained residue was ground with ether to obtain white solid spiro[isobenzodihydropyran-1,4'-piperidine] (1.35 g, 64% yield). Characterization data: 1H NMR (DMSO-d6, 400 MHz) δ: 1.88 (m, 2H), 2.09 (m, 2H), 2.77 (t, 2H), 3.02 (m, 2H), 3.15 (m, 2H), 3.90 (t, 2H), 7.10-7.28 (m, 4H). LRMS: m/z APCI+ 204 [MH]+.

References

[1] Patent: WO2006/92731, 2006, A1. Location in patent: Page/Page column 42