Hydrochloric Acid → 2-(Pyridin-4-yl)-2,9-diazaspiro[5.5]undecane dihydrochloride

HRID 1253676Notes

Reaction equation

HRID 1253676 reaction equation
[ClH:1].[N:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH2:11][C:10]3([CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)[CH2:9]2)=[CH:4][CH:3]=1>CO>[ClH:1].[ClH:1].[N:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][CH2:11][C:10]3([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66700745tert-Butyl 2-(pyridin-4-yl)-2,9-diazaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 667010972-(Pyridin-4-yl)-2,9-diazaspiro[5.5]undecane dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Hydrogen chloride in methanol (1.25 mol/l, 15.9 ml) was added to tert-butyl 2-(pyridin-4-yl)-2,9-diazaspiro[5.5]undecane-9-carboxylate (0.66 g, 1.991 mmol) and the mixture was refluxed for 2 h. The solvent was removed in vacuo, the residue was taken up in ethanol (5 ml) and the mixture was cooled. Acetone (20 ml) was added and the mixture was stirred at 0° C. for 30 min. Diethyl ether (50 ml) was added and the precipitate was filtered out with suction, washed with diethyl ether and dried in vacuo. Yield: 0.42 g (69%)

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. customThe solvent was removed in vacuo
  3. temperaturethe mixture was cooled
  4. additionAcetone (20 ml) was added
  5. additionDiethyl ether (50 ml) was added
  6. filtrationthe precipitate was filtered out with suction
  7. washwashed with diethyl ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-964957be90e743c0ab38c79e05c8a8ef
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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