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

HRID 1061290Notes

Reaction equation

HRID 1061290 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 (5mL) 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, 4H), 3.64 (t, 4H), 5.74 (s, 1H), 7.04 (d, 2H), 7.53 (d, 2H), 9.55 (brs, 1H), 11.80 (brs, 1H); 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-3b2d195dc48d432591e4078646c7df76
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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