Hydrochloric Acid → 9-Pyridin-4-yloxy-3-azaspiro[5.5]undecane dihydrochloride

HRID 1808359Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([O:7][CH:8]2[CH2:25][CH2:24][C:11]3([CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]3)[CH2:10][CH2:9]2)=[CH:3][CH:2]=1.[ClH:26]>CO>[ClH:26].[ClH:26].[N:1]1[CH:2]=[CH:3][C:4]([O:7][CH:8]2[CH2:25][CH2:24][C:11]3([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[CH2:10][CH2:9]2)=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

tert-Butyl 9-(pyridin-4-yloxy)-3-azaspiro[5.5]undecane-3-carboxylate (1 g, 2.886 mmol) was dissolved in methanol (2 ml); hydrogen chloride in methanol (1.25 mol/l, 11.5 ml) was added, and the mixture was refluxed for 30 min. The solvent was removed in vacuo and the residue was dissolved in a small amount of ethanol. Acetone (about 25 ml) was then added, the mixture was stirred for 30 min. at 0° C. and finally the resulting solid was filtered out with suction. Yield: 0.96 g (>99%)

Workup

temperaturethe mixture was refluxed for 30 min
customThe solvent was removed in vacuo
dissolutionthe residue was dissolved in a small amount of ethanol
additionAcetone (about 25 ml) was then added
filtrationfinally the resulting solid was filtered out with suction

Sources & evidence

ORD record: ord-01caebe28cf244ab8448654314ab9053
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357717B2

Reaction notes

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