Sodium Bicarbonate → 2-Methylspiro[inden-1,4'-piperidine]

HRID 1027134Notes

Reaction equation

HRID 1027134 reaction equation
FC1C=C(C=CC=1)CNC1N2N=CC(C(O)=O)=C2N=CC=1C([N:21]1[CH2:26][CH2:25][CH:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:23][CH2:22]1)=O.[C:36](=O)([O-])O.[Na+].O1[CH2:46][CH2:45]OCC1.Cl>>[CH3:36][C:45]1[C:24]2([CH2:23][CH2:22][NH:21][CH2:26][CH2:25]2)[C:27]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:46]=1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 204431481,4-Dioxane hydrochlorideHCID 675404777-(3-Fluorobenzylamino)-6-(4-phenylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

Product 1

HCID 675407632-Methylspiro[inden-1,4'-piperidine]Yield 72%

Procedure

tert-Butyl 2-methylspiro[inden-1,4′-piperidine]-1′-carboxylate (1.19 g, 3.98 mmol) obtained in step 2 was dissolved in 4 mol/L hydrogen chloride-1,4-dioxane (6 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the obtained residue, and the mixture was suction-filtered to give white crystals. Saturated aqueous sodium hydrogen carbonate solution was added to the white crystals, and the mixture was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, and concentrated under reduced pressure to give the title compound (0.790 g, 72%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate
  2. additionwas added to the obtained residue
  3. filtrationthe mixture was suction-filtered
  4. customto give white crystals
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2539ba4e1cb44a0d84972f20dd1afdd2
Source dataset
uspto-grants-2014_05
Patent number
US08729264B2

Reaction notes

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