Water → HCID 22911473, compound

HRID 1780798Notes

Reaction equation

HRID 1780798 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([C:13](=O)[CH:14]=[C:15](O)[C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[CH3:27][NH:28][NH2:29].CN(C=O)C.O>CO>[CH3:27][N:28]1[C:13]([CH:10]2[CH2:11][CH2:12][N:7]([CH2:6][C:5]3[CH:25]=[CH:26][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH2:8][CH2:9]2)=[CH:14][C:15]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[N:29]1

Participants

6

Reactant 4

HCID 962WaterHCID 6061MethylhydrazineHCID 6228DimethylformamideHCID 67015285HCID 67015285, compound

Product 1

HCID 22911473HCID 22911473, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(4-Chlorobenzyl)-4-(3-hydroxy-1-oxo-3-(4-chlorophenyl)-prop-2-en-1-yl)piperidine obtained from Example 1 (264 mg) and methyl hydrazine (62 mg) were stirred in methanol (5 ml) and DMF (2 ml) for 16 h. Water was added, the mixture extracted with ethyl acetate (3×20 ml), the combined organic layers washed with water and brine, dried (MgSO4), evaporated in vacuo, and purified by preparative thin layer chromatography, eluding with dichloromethane:methanol: triethylamine (98:2:1 v/v) to give 1-methyl-5-(1-(4-chlorobenzyl)-4-piperidinyl)-3-(4-chlorophenyl)pyrazole (93 mg): oxalate salt.

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×20 ml)
  2. washthe combined organic layers washed with water and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. custompurified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-f9cb6f4351b24affaae6c1ad2295812e
Source dataset
uspto-grants-1997_05
Patent number
US05631269

Reaction notes

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