Hydrochloric Acid → 7-[(5-Methoxypyridin-2-yl)acetyl]-2,7-diazaspiro-[3.5]nonane dihydrochloride

HRID 1913449Notes

Reaction equation

HRID 1913449 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([N:12]2[CH2:27][CH2:26][C:15]3([CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16]3)[CH2:14][CH2:13]2)=[O:11])=[N:7][CH:8]=1.[ClH:28]>O1CCOCC1.C(OCC)(=O)C>[ClH:28].[ClH:28].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([N:12]2[CH2:13][CH2:14][C:15]3([CH2:18][NH:17][CH2:16]3)[CH2:26][CH2:27]2)=[O:11])=[N:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58438449tert-Butyl 7-[(5-methoxypyridin-2-yl)acetyl]-2,7-diazaspiro[3.5]nonane-2-carboxylate

Product 1

HCID 674075527-[(5-Methoxypyridin-2-yl)acetyl]-2,7-diazaspiro-[3.5]nonane dihydrochlorideYield 78%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl 7-[(5-methoxypyridin-2-yl)acetyl]-2,7-diazaspiro[3.5]nonane-2-carboxylate (2-1a, 2.57 g, 6.85 mmol) in dioxane (5 mL) was added 4N HCl in dioxane (1.72 mL). The mixture was stirred at room temperature for 5 hours and heated at 45° C. overnight. The light-yellow mixture was concentrated to give a light-yellow sticky foam. The residue was suspended in ethyl acetate and evaporated to dryness (3×) to afford the title compound (2-1b, 1.86 g, 78%) MS (ES+) 276.4 (M+H)+. 1H NMR (CD3OD) δ 2.17-2.42 (m, 2H), 2.48 (d, 2H), 3.94-4.13 (m, 4H), 4.40 (d, 4H), 4.51 (s, 3H), 4.74 (s, 2H), 8.34 (d, 1H), 8.61-8.64 (m, 1H), 8.99-9.01 (m 1H).

Workup

  1. temperatureheated at 45° C. overnight
  2. concentrationThe light-yellow mixture was concentrated
  3. customto give a light-yellow sticky foam
  4. customevaporated to dryness (3×)

Sources & evidence

ORD record
ord-a2e2fe1a7b504165b8a7f4134bf2f36f
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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