Hydrochloric Acid → HCID 58137269, compound

HRID 1424573Notes

Reaction equation

HRID 1424573 reaction equation
C([N:9]1[CH2:14][CH2:13][CH2:12][C:11]2([CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:23])[CH2:10]1)(=O)C1C=CC=CC=1.Cl>CO>[NH:9]1[CH2:14][CH2:13][CH2:12][C:11]2([CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:23])[CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58137244HCID 58137244, compound

Product 1

HCID 58137269HCID 58137269, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1′-benzoylspiro[indene-2,3′-piperidin]-1(3H)-one (2.476 g, 8.11 mmol) was dissolved in methanol (40 mL). 1 N aq HCl (80 mL) was added dropwise and the mixture was refluxed overnight. The methanol was removed in vacuo. The pH of the solution was adjusted to 8 using saturated Na2CO3, and the solution was extracted with CH2Cl2. The combined organic extracts were dried over anhydrous Na2SO4 and then concentrated to afford a residue, which was purified by silica gel column chromatography to afford spiro[indene-2,3′-piperidin]-1(3H)-one (460 mg, 28%). 1H NMR (CD3OD, 400 MHz): δ=1.63 (m, 2H), 1.82 (m, 1H), 1.87-2.00 (m, 1H), 2.70 (d, 1H), 2.82 (m, 1H), 3.00 (m, 3H), 3.20 (d, 1H), 7.32 (m, 1H), 7.45 (m, 1H), 7.57 (m, 1H), 7.79 (m, 1H).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customThe methanol was removed in vacuo
  3. extractionthe solution was extracted with CH2Cl2
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto afford a residue, which
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a3f8d41a10474865921671a4e531b182
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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