Hydrochloric Acid → 2,9-Diazaspiro(5.5)undecan-1-one hydrochloride

HRID 41538Notes

Reaction equation

HRID 41538 reaction equation
[O:1]=[C:2]1[C:7]2([CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][NH:3]1.[ClH:20]>C(Cl)Cl.O1CCOCC1>[ClH:20].[C:2]1(=[O:1])[C:7]2([CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][NH:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 49760149tert-Butyl 1-oxo-2,9-diazaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 450742882,9-Diazaspiro(5.5)undecan-1-one hydrochlorideYield 96%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To the stirred solution of tert-butyl 1-oxo-2,9-diazaspiro[5.5]undecane-9-carboxylate (3.0 g, 11.19 mmol) in DCM (60 mL) was added 4N HCl in dioxane (20 mL) and the mixture was stirred at rt for 18 h. The solvent was removed under reduced pressure and triturated with diethyl ether (2×5 mL) to yield the title compound as a solid (2.2 g, 96%). Note: The product is moisture sensitive. [1H-NMR (DMSO-d6, 300 MHz): δ 9.25-8.68 (m, 2H), 7.43 (s, 1H), 7.20-6.25 (m, 2H), 3.61-2.90 (m, 5H), 2.12-1.95 (m, 2H), 1.76-1.49 (m, 5H); LCMS RtA=0.326, [M+H]+=169.0].

Workup

  1. customThe solvent was removed under reduced pressure
  2. customtriturated with diethyl ether (2×5 mL)

Sources & evidence

ORD record
ord-67defb743249464596a605a19e4e499a
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Reaction notes

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