Hydrochloric Acid → Benzyl 2,9-diazaspiro[5.5]undecane-2-carboxylate hydrochloride

HRID 2284872Notes

Reaction equation

HRID 2284872 reaction equation
[CH2:1]1[C:6]2([CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]2)[CH2:5][N:4]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:3][CH2:2]1.O1CCOCC1.[ClH:35]>CC(OC)(C)C>[ClH:35].[CH2:1]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:5][N:4]([C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 118049948O2-benzyl O9-tert-butyl 2,9-diazaspiro[5.5]undecane-2,9-dicarboxylate

Product 1

HCID 118045112Benzyl 2,9-diazaspiro[5.5]undecane-2-carboxylate hydrochlorideYield 95.3%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a 20 L temperature controlled reactor with jacket set at 0° C., add a solution of O4-benzyl O9-tert-butyl 4,9-diazaspiro[5.5]undecane-4,9-dicarboxylate (2.06 moles; 838.00 g; 95.65% purity) in 1,4-dioxane (19.63 moles; 1.68 L). When the temperature of the solution is 5° C., add hydrogen chloride (4 M in 1,4-dioxane; 10.32 moles; 2.58 L) at such a rate that the temperature does not rise above 20° C. When the addition is complete, warm the solution to room temperature and stir overnight. Concentrate the reaction mixture under reduced pressure to give a thick slurry. Add MTBE (3.35 L) and agitate the mixture for 30 minutes at 40° C. Allow the mixture to cool to room temperature and filter the precipitate. Wash the precipitate with MTBE (838 mL). Allow the precipitate to dry on the filter and then transfer to a vacuum oven for further drying to give the title compound (638 g; 95% yield) mass spectrum (m/z):289 [M(freebase)+1].

Workup

  1. customset at 0° C.
  2. customis 5° C.
  3. customdoes not rise above 20° C
  4. additionWhen the addition
  5. concentrationConcentrate the reaction mixture under reduced pressure
  6. customto give a thick slurry
  7. temperatureAllow the mixture to cool to room temperature
  8. filtrationfilter the precipitate
  9. washWash the precipitate with MTBE (838 mL)
  10. customto dry on the
  11. filtrationfilter
  12. customfor further drying

Sources & evidence

ORD record
ord-184db9b30fbf40da942e0e498a63d2ec
Source dataset
uspto-grants-2015_09
Patent number
US09145437B2

Reaction notes

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