Hydrochloric Acid → 8-Benzyl-8-azaspiro[4,5]decane-6-carboxylic acid methyl ester

HRID 1815825Notes

Reaction equation

Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][C:12](=O)[CH:11]([C:16]([O:18][CH3:19])=[O:17])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.[OH-].[Na+]>C(O)CO>[CH3:19][O:18][C:16]([CH:11]1[CH2:10][N:9]([CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:14][CH2:13][C:12]21[CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:17]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 20.0 gm (70.4 mMol) 1-benzyl-3-methoxycarbonyl-4-oxopiperidine hydrochloride in 60 mL ethylene glycol was cooled in an ice bath as 24 gm hydrogen chloride were added. The slurry was heated at 70° C. for 2 hours and was then poured into 200 mL ice water. The pH was adjusted to about 8 with 5N sodium hydroxide and the resulting mixture extracted well with diethyl ether. The organic extracts were combined, dried over sodium sulfate, and concentrated under reduced pressure to provide 21 gm 8-benzyl-8-azaspiro[4,5]decane-6-carboxylic acid methyl ester.

Workup

additionwere added
extractionthe resulting mixture extracted well with diethyl ether
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-0c4135486f214757ac55b92f3927734a
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06881733B1

Reaction notes

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