Potassium Carbonate → HCID 71285281, compound

HRID 1182689Notes

Reaction equation

HRID 1182689 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]1[C:10]2([CH2:13][NH:12][CH2:11]2)[CH2:9][NH:8]1.Cl[C:15]1[N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:18]=[N:17][N:16]=1>C(O)C>[C:20]1([N:19]2[C:15]([N:8]3[CH2:9][C:10]4([CH2:13][NH:12][CH2:11]4)[CH2:7]3)=[N:16][N:17]=[N:18]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 842621H-Tetrazole, 5-chloro-1-phenyl-HCID 216924042,6-Diazaspiro[3.3]heptane

Product 1

HCID 71285281HCID 71285281, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To potassium carbonate (76 mg) taken in ethanol (2.0 mL), a solution of 2,6-diazaspiro[3.3]heptane (220 mg in 2.0 ml of ethanol) was added at room temperature. The reaction mixture was stirred for 30 minutes at room temperature and a solution of 5-chloro-1-phenyl tetrazole (0.1 g) in ethanol (2.0 mL) was added very slowly. The reaction mixture was allowed to stir for 5 hours at room temperature. The reaction mixture was evaporated to give a residue which was partitioned between water (10 mL) and EtOAc (20 mL). The aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure gave crude product which was purified by column chromatography using methanol\dichloromethane (1:9) as eluent to afford 2-(1-phenyl-1H-tetrazol-5-yl)-2,6-diazaspiro[3.3]heptane (50 mg).

Workup

  1. stirringto stir for 5 hours at room temperature
  2. customThe reaction mixture was evaporated
  3. customto give a residue which
  4. customwas partitioned between water (10 mL) and EtOAc (20 mL)
  5. extractionThe aqueous layer was extracted with ethyl acetate (3×20 mL)
  6. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customgave crude product which
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-69470f111cff4610b8592d9725bbadc0
Source dataset
uspto-grants-2014_03
Patent number
US08664213B2

Reaction notes

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