5-chlorospiro[chroMan-2,4'-piperidine] hcl synthesis

7synthesis methods

Product Name:5-chlorospiro[chroMan-2,4'-piperidine] hcl
CAS Number:1241953-54-7
Molecular formula:C13H17Cl2NO
Molecular Weight:274.19

Spiro[2H-1-benzopyran-2,4'-piperidine], 5-chloro-3,4-dihydro-

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5-chlorospiro[chroMan-2,4'-piperidine] hcl

1241953-54-7
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Yield:-

Reaction Conditions:

with hydrogenchloride in diethyl ether;

Steps:

1.4

To a mixture of tert-butyl 5-chloro-4-hydroxy-3,4-dihydro-1'H-spiro[chromene-2,4'-piperidine]-1'-carboxylate (12.4 g, 35.04 mmol, 1.00 equiv) in trifluoroacetic acid (130 mL) was added triethylsilane (16.8 g, 144.48 mmol, 4.12 equiv). The resulting mixture was allowed to react, with stirring, for 5 h while the temperature was maintained at 80 °C to reflux. The resulting mixture was concentrated under vacuum. To the resulting residue were added 200 mL of Et₂O. The resulting solids were collected by filtration to give the TFA salt as a white solid. The TFA salt was converted to the free base by the treatment with aqueous NaOH. The free base was then dissolved in Et₂O and reacted with HCl gas to give the title compound as a white solid

References:

WO2011/47481,2011,A1 Location in patent:Page/Page column 54

108-43-0 Synthesis