Hydrazine hydrate (1:1) → HCID 178461462, compound

HRID 657635Notes

Reaction equation

HRID 657635 reaction equation
[CH3:1][C@H:2]1[CH2:7][C@H:6]([CH3:8])[CH2:5][N:4]([CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19](=O)[CH2:20][CH:21]=O)=[CH:15][CH:14]=2)[CH2:3]1.O.[NH2:25][NH2:26]>CO.O>[CH3:1][C@H:2]1[CH2:7][C@H:6]([CH3:8])[CH2:5][N:4]([CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]=[CH:21][NH:26][N:25]=3)=[CH:15][CH:14]=2)[CH2:3]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86629974HCID 86629974, compound

Product 1

HCID 178461462HCID 178461462, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of trans-3,5-dimethyl-1-{3-[4-(3-oxopropanoyl)phenoxy]propyl}-piperidine (200 mg) in a mixture of hydrazine hydrate (50 μL) and methanol (4 mL) is stirred for one hour at room temperature. The mixture is diluted with water and extracted twice with ethyl acetate, dried over magnesium sulphate, concentrated under reduced pressure and purified by chromatography over silica gel. Fractions containing the expected product are pooled, concentrated under reduced pressure and salted with oxalic acid to afford 142 mg of trans-3,5-dimethyl-1-{3-[4-(pyrazol-3-yl)phenoxy]propyl}piperidine, oxalate as a pale yellow solid.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. custompurified by chromatography over silica gel
  5. additionFractions containing the expected product
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c06562a4b9a64dfe816a532b26eaddf7
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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