Potassium Carbonate → 8-(3-Aminopropyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one

HRID 964264Notes

Reaction equation

HRID 964264 reaction equation
[C:1]1([N:7]2[C:11]3([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:10](=[O:17])[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br.Br[CH2:20][CH2:21][CH2:22][NH2:23].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[NH2:23][CH2:22][CH2:21][CH2:20][N:14]1[CH2:13][CH2:12][C:11]2([N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8][NH:9][C:10]2=[O:17])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 787013-Bromopropylamine hydrobromide

Product 1

HCID 230041328-(3-Aminopropyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-oneYield 4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1-Phenyl-1,3,8-triazaspiro[4.5]decan-4-one (5.00 g, 21.6 mol, 1.00 equiv), 3-bromopropylamine hydrobromide (4.73 g, 21.6 mmol, 1.00 equiv) and potassium carbonate (2.99 g, 21.6 mmol, 1.00 equiv) were stirred in refluxing dioxane (70 mL) for 24 hours. After removal of the solvent, water (50 mL) was added and the pH was adjusted to 11-12 by addition of 1N aqueous NaOH. The mixture was extracted with CH2Cl2 (200 mL+3×100 mL). The combined organic solutions were dried over MgSO4 and concentrated. The residue was purified by flash chromatography (SiO2, CHCl3 -MeOH-NH3 (2M in MeOH) 100:20:10 to 100:24:12) to give 250 mg (4%) of white solid, which was characterized spectroscopically.

Workup

  1. customAfter removal of the solvent, water (50 mL)
  2. additionwas added
  3. additionthe pH was adjusted to 11-12 by addition of 1N aqueous NaOH
  4. extractionThe mixture was extracted with CH2Cl2 (200 mL+3×100 mL)
  5. dry with materialThe combined organic solutions were dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (SiO2, CHCl3 -MeOH-NH3 (2M in MeOH) 100:20:10 to 100:24:12)

Sources & evidence

ORD record
ord-352a47de481e4100bb1f7abf28d2053f
Source dataset
uspto-grants-1998_06
Patent number
US05767131

Reaction notes

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