Hydrochloric Acid → 3-Methyl-3,9-diazaspiro[5.5]undecane dihydrochloride

HRID 501960Notes

Reaction equation

HRID 501960 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][N:16](C)[CH2:15][CH2:14]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[ClH:20].[H][H]>C(O)C.[Pd]>[ClH:20].[ClH:20].[CH3:1][N:8]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 218132923-Benzyl-9-methyl-3,9-diazaspiro[5.5]undecaneHCID 178418361HCID 178418361, compound

Product 1

HCID 675237033-Methyl-3,9-diazaspiro[5.5]undecane dihydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-Benzyl-9-methyl-3,9-diaza-spiro[5.5]undecane (Rice, L. M. et al. J Heterocyclic Chem. 1964, 1, 3, 125.) (1.2 g, 4.65 mmol) was dissolved in ethanol (20 mL). To this solution was added hydrochloric acid (4 N in dioxane, 3 mL) and palladium (10% on charcoal, 500 mg). The reaction was shaken on a Parr shaker overnight under 60 psi of hydrogen. The reaction mixture was filtered through a pad of celite, concentrated, and the residue treated with a mixture of ethyl acetate and hexanes, to yield 670 mg (60%) as a white powder. 1H-NMR (CD3OD) δ 1.68-1.72 (m, 4H), 2.88 (s, 3H), 3.16-3.22 (m, 6H), 3.38 (m, 2H). Mass spec.: 169.12 (MH)+.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationconcentrated
  3. additionthe residue treated with a mixture of ethyl acetate and hexanes
  4. customto yield 670 mg (60%) as a white powder

Sources & evidence

ORD record
ord-fdcd3908f97242c888e4679eb9447e9d
Source dataset
uspto-grants-2010_08
Patent number
US07772244B2

Reaction notes

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