Water → 1-[4-(5-Oxo-2,5-dihydro-1H-pyrazol-3-yl)-phenyl]-piperidin-4-one

HRID 1794795Notes

Reaction equation

HRID 1794795 reaction equation
O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([C:17]4[NH:21][NH:20][C:19](=[O:22])[CH:18]=4)=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:4]CC1.S(=O)(=O)(O)O.O>CC(C)=O>[O:22]=[C:19]1[NH:20][NH:21][C:17]([C:14]2[CH:15]=[CH:16][C:11]([N:8]3[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]3)=[CH:12][CH:13]=2)=[CH:18]1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 22220325HCID 22220325, compound

Product 1

HCID 222204011-[4-(5-Oxo-2,5-dihydro-1H-pyrazol-3-yl)-phenyl]-piperidin-4-oneYield 116.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 5-[4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-phenyl]-1,2-dihydro-pyrazol-3-one (which was obtained in Example 144) (0.15 g, 0.5 mmol) in acetone (5 mL) was added 5 mL of 10% sulfuric acid. The resulting solution was stirred at room temperature for 4 days. Water (5 mL) was then added, and the acetone was evaporated. The aqueous residue was treated with sodium carbonate until pH 8, and the resulting suspension was filtered. The precipitate was washed with water and ether, and dried in vacuo to give 0.15 g of tan solid; 1H NMR (DMSO-d6) δ 2.41 (t, 4 H), 3.64 (t, 4 H), 5.74 (s, 1 H), 7.04 (d, 2 H), 7.53 (d, 2 H), 9.55 (brs, 1 H), 11.80 (brs, 1 H); MS (ES) m/z: 258 (MH+).

Workup

  1. customthe acetone was evaporated
  2. additionThe aqueous residue was treated with sodium carbonate until pH 8
  3. filtrationthe resulting suspension was filtered
  4. washThe precipitate was washed with water and ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ae99f5bfbc7144aabd698ed40637777c
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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