Water → HCID 9847850, compound

HRID 369189Notes

Reaction equation

HRID 369189 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH:13]1[CH2:18][CH2:17][N:16]([C:19](=[O:32])[C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH:30]=[N:29][CH:28]=[N:27]3)=[C:22]([OH:31])[CH:21]=2)[CH2:15][CH2:14]1)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl[CH2:34][CH2:35][N:36]([CH3:38])[CH3:37].O>CN(C)C=O>[CH3:3][N:4]([CH:13]1[CH2:18][CH2:17][N:16]([C:19](=[O:32])[C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH:30]=[N:29][CH:28]=[N:27]3)=[C:22]([O:31][CH2:34][CH2:35][N:36]([CH3:38])[CH3:37])[CH:21]=2)[CH2:15][CH2:14]1)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 23285059HCID 23285059, compound

Product 1

HCID 9847850HCID 9847850, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

120 mg of sodium hydride was added, under ice-cooling, to a solution of 1.0 g of 4-[N-methyl-N-(2-phenylethyl)amino]-1-[3-hydroxy-4-(1,2,4-triazol-1-yl)benzoyl]piperidine in 10 ml of dimethylformamide. The mixture was stirred for 1 hour. Thereto was dropwise added 320 mg of (2-chloroethyl)dimethylamine. The mixture was stirred at room temperature for 2 hours and then at 50° C. for 2 hours. The reaction mixture was poured into 50 ml of water. The mixture was extracted with three 50-ml portions of ethyl acetate. The extract was washed with 50 ml of a saturated aqueous sodium chloride solution, dried with magnesium sulfate, and subjected to distillation to remove the solvent. The residue was purified by a silica gel column chromatography (eluant: dichloromethane/methanol=10/1 to dichloromethane/methanol/ammonia water=100/10/1). The product was recrystallized from ethyl acetate-n-hexane to obtain 500 mg of 4-[N-methyl-N-(2-phenylethyl)amino]-1-[3-(2-dimethylaminoethoxy)-4-(1,2,4-triazol-1-yl)benzoyl]piperidine as a white powder.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. waitat 50° C. for 2 hours
  3. extractionThe mixture was extracted with three 50-ml portions of ethyl acetate
  4. washThe extract was washed with 50 ml of a saturated aqueous sodium chloride solution
  5. dry with materialdried with magnesium sulfate
  6. distillationsubjected to distillation
  7. customto remove the solvent
  8. customThe residue was purified by a silica gel column chromatography (eluant: dichloromethane/methanol=10/1 to dichloromethane/methanol/ammonia water=100/10/1)
  9. customThe product was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-b462f55a01664d02865e122b55bb4234
Source dataset
uspto-grants-2000_10
Patent number
US06136826

Reaction notes

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