N-Piperidinoethanol → HCID 10228358, compound

HRID 1727890Notes

Reaction equation

HRID 1727890 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([C:14]([NH:16][CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:15])=[C:12]([CH3:26])[N:11]=[C:10](SC)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.ClC1C=CC=C(C(OO)=O)C=1.S(=O)(O)[O-].[Na+].[N:45]1([CH2:51][CH2:52][OH:53])[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1.[H-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([C:14]([NH:16][CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:15])=[C:12]([CH3:26])[N:11]=[C:10]([O:53][CH2:52][CH2:51][N:45]3[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 18232N-PiperidinoethanolHCID 24758Sodium hydrideHCID 70297m-Chloroperbenzoic acidHCID 17854639HCID 17854639, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 10228358HCID 10228358, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

185 mg (0.254 mmol) of 4-(3-chlorophenyl)-6-methyl-2-(methylthio)-N-(3-phenylpropyl)-5-pyrimidinecarboxamide was dissolved in 5 ml of dichloromethane. 87.7 mg (0.508 mmol) of mCPBA (m-chloroperbenzoic acid) was added thereto at 0° C. and stirred at the same temperature for 6 hours. 1 ml of saturated aqueous sodium bisulfite solution was added thereto at the same temperature and stirred for 30 minutes heating to room temperature. After the reaction mixture was diluted with dichloromethane, the organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was dissolved in 5 ml of DMF. Alkoxide prepared from 146 mg (1.13 mmol) of 1-piperidine ethanol and 45.2 mg (1.13 mmol) of sodium hydride (60% oily substance) was added at 0° C. and stirred heating to room temperature for 1 hour. After concentration under reduced pressure, the obtained residue was diluted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the basic silica gel chromatography (hexane/ethyl acetate=5/1 to 1/1) to obtain the title compound.

Workup

  1. stirringat the same temperature and stirred for 30 minutes
  2. temperatureheating to room temperature
  3. washthe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe obtained residue was dissolved in 5 ml of DMF
  7. additionwas added at 0° C.
  8. stirringstirred
  9. temperatureheating to room temperature for 1 hour
  10. concentrationAfter concentration under reduced pressure
  11. additionthe obtained residue was diluted with ethyl acetate
  12. washThe organic layer was washed with saturated aqueous sodium chloride solution
  13. dry with materialdried over anhydrous magnesium sulfate
  14. concentrationconcentrated under reduced pressure
  15. customThe residue was purified by the basic silica gel chromatography (hexane/ethyl acetate=5/1 to 1/1)

Sources & evidence

ORD record
ord-2bd163ca9f00438baf39e311c5a2fd22
Source dataset
uspto-grants-2009_02
Patent number
US07494989B2

Reaction notes

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